Asymmetric Hydroesterification of Diarylmethyl Carbinols
Duanshuai Tian
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
Search for more papers by this authorRonghua Xu
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
Search for more papers by this authorJinbin Zhu
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
Search for more papers by this authorJianxun Huang
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
Search for more papers by this authorWei Dong
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Jerome Claverie
Department of Chemistry, University of Sherbrooke, 2500 Blvd de l'Université, Sherbrooke, Qc, J1K2R1 Canada
Search for more papers by this authorCorresponding Author
Prof. Dr. Wenjun Tang
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, 1 Sub-lane Xiangshan, Hangzhou, 310024 China
Search for more papers by this authorDuanshuai Tian
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
Search for more papers by this authorRonghua Xu
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
Search for more papers by this authorJinbin Zhu
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
Search for more papers by this authorJianxun Huang
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
Search for more papers by this authorWei Dong
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Jerome Claverie
Department of Chemistry, University of Sherbrooke, 2500 Blvd de l'Université, Sherbrooke, Qc, J1K2R1 Canada
Search for more papers by this authorCorresponding Author
Prof. Dr. Wenjun Tang
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai, 200032 China
School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, 1 Sub-lane Xiangshan, Hangzhou, 310024 China
Search for more papers by this authorAbstract
An efficient asymmetric hydroesterfication of diarylmethyl carbinols is developed for the first time with a Pd-WingPhos catalyst, resulting in a series of chiral 4-aryl-3,4-dihydrocoumarins in excellent enantioselectivities and good yields. The method features mild reaction conditions, a broad substrate scope, use of easily accessible starting materials, and low palladium loadings. A plausible stereochemical model is also proposed with the Pd-WingPhos catalyst. This method has enabled a 4-step asymmetric synthesis of (R)-tolterodine from readily available starting materials.
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References
- 1For selected reviews, see:
- 1aG. Kiss, Chem. Rev. 2001, 101, 3435;
- 1bL. Kollár, Modern Carbonylation Methods, Wiley-VCH, Weinheim, 2008;
10.1002/9783527621545 Google Scholar
- 1cM. Beller, X.-F. Wu, Transition Metal Catalyzed Carbonylation Reactions, Springer, Berlin, 2013;
10.1007/978-3-642-39016-6 Google Scholar
- 1dS. Quintero-Duque, K. M. Dyballa, I. Fleischer, Tetrahedron Lett. 2015, 56, 2634;
- 1eP. H. Gehrtz, V. Hirschbeck, B. Ciszek, I. Fleischer, Synthesis 2016, 48, 1573;
- 1fX.-F. Wu, H. Neumann, M. Beller, Chem. Rev. 2013, 113, 1;
- 1gW. Fang, H. Zhu, Q. Deng, S. Liu, X. Liu, Y. Shen, T. Tu, Synthesis 2014, 46, 1689;
- 1hC. F. J. Barnard, Organometallics 2008, 27, 5402;
- 1iY. Bai, D. C. Davis, M.-J. Dai, J. Org. Chem. 2017, 82, 2319–2328.
- 2For recent representative works, see:
- 2aH. Li, K. Dong, H. Jiao, H. Neumann, R. Jackstell, M. Beller, Nat. Chem. 2016, 8, 1159–1166;
- 2bK. Dong, X. Fang, R. Franke, A. Spannenberg, H. Neumann, R. Jackstell, M. Beller, Nat. Commun. 2017, 8, 14117;
- 2cJ. Yang, J. Liu, H. Neumann, R. Franke, R. Jackstell, M. Beller, Science 2019, 366, 1514–1517;
- 2dJ. Liu, J. Yang, W. Baumann, R. Jackstell, M. Beller, Angew. Chem. Int. Ed. 2019, 58, 10683–10687; Angew. Chem. 2019, 131, 10793–10797;
- 2eJ. Liu, K. Dong, R. Franke, H. Neumann, R. Jackstell, M. Beller, J. Am. Chem. Soc. 2018, 140, 10282–10288;
- 2fJ. Liu, J. Yang, C. Schneider, R. Franke, R. Jackstell, M. Beller, Angew. Chem. Int. Ed. 2020, 59, 9032–9040; Angew. Chem. 2020, 132, 9117–9125;
- 2gF. Sha, H. Alper, ACS Catal. 2017, 7, 2220–2229;
- 2hJ. Chen, M. Huang, W. Ren, J. Chu, Y. Shi, Eur. J. Org. Chem. 2020, 1078–1083.
- 3
- 3aI. Ryu, Chem. Soc. Rev. 2001, 30, 16;
- 3bK. Dong, R. Sang, J. Liu, R. Razzaq, R. Franke, R. Jackstell, M. Beller, Angew. Chem. Int. Ed. 2017, 56, 6203–6207; Angew. Chem. 2017, 129, 5351–5355.
- 4For reviews, see:
- 4aC. Godard, K. B. Muñoz, A. Ruiz, C. Claver, Dalton Trans. 2008, 853–860;
- 4bC. Godard, B. F. Perandones, A. Gual, C. Claver in Comprehensive Inorganic Chemistry II, 2nd ed. (Ed.: J. Reedijk, K. Poeppelmeier), Elsevier, Amsterdam, 2013, pp. 383–411.
10.1016/B978-0-08-097774-4.00615-X Google Scholar
- 5For leading references on Pd-catalyzed asymmetric intermolecular hydroesterification of olefins with CO gas, see:
- 5aG. Consiglio, Helv. Chim. Acta 1976, 59, 124;
- 5bT. Hayashi, M. Tanaka, I. Ogata, Tetrahedron Lett. 1978, 19, 3925;
10.1016/S0040-4039(01)95099-3 Google Scholar
- 5cG. Cometti, G. P. Chiusoli, J. Organomet. Chem. 1982, 236, C31;
- 5dG. Chelucci, M. A. Cabras, C. Botteghi, M. Marchetti, Tetrahedron: Asymmetry 1994, 5, 299;
- 5eH. Zhou, S. Lu, J. Hou, J. Chen, H. Fu, H. Wang, Chem. Lett. 1996, 25, 339;
- 5fH. Zhou, J. Hou, J. Cheng, S. Lu, H. Fu, H. Wang, J. Organomet. Chem. 1997, 543, 227;
- 5gS. Oi, M. Nomura, T. Aiko, Y. Inoue, J. Mol. Catal. A 1997, 115, 289;
- 5hK. Nozaki, M. L. Kantam, T. Horiuchi, H. Takaya, J. Mol. Catal. A 1997, 118, 247;
- 5iL. Wang, W. H. Kwok, A. S. C. Chan, T. Tu, X. Hou, L. Dai, Tetrahedron: Asymmetry 2003, 14, 2291;
- 5jY. Kawashima, K. Okano, K. Nozaki, T. Hiyama, Bull. Chem. Soc. Jpn. 2004, 77, 347;
- 5kB. Muñoz, A. Marinetti, A. Ruiz, S. Castillon, C. Claver, Inorg. Chem. Commun. 2005, 8, 1113;
- 5lE. Guiu, M. Caporali, B. Muñoz, C. Müller, M. Lutz, A. L. Spek, C. Claver, P. W. N. M. van Leeuwen, Organometallics 2006, 25, 3102;
- 5mC. Godard, A. Ruiz, C. Claver, Helv. Chim. Acta 2006, 89, 1610;
- 5nB. K. Muñoz, C. Godard, A. Marinetti, A. Ruiz, J. Benet-Buchholz, C. Claver, Dalton Trans. 2007, 5524;
- 5oJ. Li, W. Chang, C. Ren, J. Dai, Y. Shi, Org. Lett. 2016, 18, 5456–5459;
- 5pJ. Li, W. Ren, J. Dai, Y. Shi, Org. Chem. Front. 2018, 5, 75–79.
- 6For leading references on Pd-catalyzed asymmetric intermolecular hydroxycarbonylation of olefins with CO gas, see:
- 6aC. Botteghi, G. Consiglio, P. Pino, Chimia 1973, 27, 477;
- 6bG. Consiglio, J. Organomet. Chem. 1977, 132, C26;
- 6cY. Becker, A. Eisenstadt, J. K. Stille, J. Org. Chem. 1980, 45, 2145;
- 6dH. Alper, N. Hamel, J. Am. Chem. Soc. 1990, 112, 2803;
- 6eM. D. Miquel-Serrano, A. Aghmiz, M. Dieguez, A. M. Masdeu-Bulto, C. Claver, D. Sinou, Tetrahedron: Asymmetry 1999, 10, 4463;
- 6fT. M. Konrad, J. A. Fuentes, A. M. Z. Slawin, M. L. Clarke, Angew. Chem. Int. Ed. 2010, 49, 9197–9200; Angew. Chem. 2010, 122, 9383–9386;
- 6gT. M. Konrad, J. T. Durrani, C. J. Cobley, M. L. Clarke, Chem. Commun. 2013, 49, 3306.
- 7For leading references on Pd-catalyzed intramolecular hydroesterification of olefins with CO gas, see:
- 7aJ. Li, W. Chang, W. Ren, W. Liu, H. Wang, Y. Shi, Org. Biomol. Chem. 2015, 13, 10341–10347;
- 7bC. Dong, H. Alper, J. Org. Chem. 2004, 69, 5011–5014;
- 7cW. Yu, C. Bensimon, H. Alper, Chem. Eur. J. 1997, 3, 417–423;
- 7dB. El Ali, K. Okuro, G. Vasapollo, H. Alper, J. Am. Chem. Soc. 1996, 118, 4264–4270.
- 8
- 8aJ. R. S. Hoult, M. Paya, Gen. Pharmacol. 1996, 27, 713–722;
- 8bD. Yu, M. Suzuki, L. Xie, S. L. Morris-Natschke, K. H. Lee, Med. Res. Rev. 2003, 23, 322–345;
- 8cP. T. Thuong, T. M. Hung, T. M. Ngoc, D. T. Ha, B. S. Min, S. J. Kwack, K. Bae, Phytother. Res. 2010, 24, 101–106;
- 8dA. Gliszczyńska, P. E. Brodelius, Phytochem. Rev. 2012, 11, 77–96;
- 8eX. Sun, A. T. Sneden, Planta Med. 1999, 65, 671–673;
- 8fB. T. Ngadjui, G. W. F. Kapche, H. Tamboue, B. M. Abegaz, J. D. Connolly, Phytochemistry 1999, 51, 119–123;
- 8gM. Iinuma, T. Tanaka, M. Takenaka, M. Mizuno, F. Asai, Phytochemistry 1992, 31, 2487–2490;
- 8hX. M. Li, M. Lin, Y. H. Wang, X. Liu, Planta Med. 2004, 70, 160–165;
- 8iS. Xu, M. Y. Shang, G. X. Liu, F. Xu, X. Wang, C. C. Shou, S. Q. Cai, Molecules 2013, 18, 5265–5287;
- 8jN. Tabanca, R. S. Pawar, D. Ferreira, J. P. Marais, S. I. Khan, V. Joshi, I. A. Khan, Planta Med. 2007, 73, 1107–1111;
- 8kM. Takechi, Y. Tanaka, M. Takehara, G. I. Nonaka, I. Nishioka, Phytochemistry 1985, 24, 2245–2250;
- 8lK. V. Sashidhara, S. P. Singh, S. V. Singh, R. K. Srivastava, K. Srivastava, J. K. Saxena, S. K. Puri, Eur. J. Med. Chem. 2013, 60, 497–502;
- 8mQ. Xiong, W. Fan, Y. Tezuka, I. K. Adnyana, P. Stampoulis, M. Hattori, T. Namba, S. Kadota, Planta Med. 2000, 66, 127–133.
- 9J. R. Huh, E. E. Englund, H. Wang, R. Huang, P. Huang, F. Rastinejad, D. R. Littman, ACS Med. Chem. Lett. 2013, 4, 79–84.
- 10F. Song, S. Lu, J. Gunnet, J. Z. Xu, P. Wines, J. Proost, Y. Liang, C. Baumann, J. Lenhard, W. V. Murray, K. T. Demarest, G. Kuo, J. Med. Chem. 2007, 50, 2807.
- 11
- 11aJ. R. Gage, J. E. Cabaj, U.S. Patent 1,996,003,396, 1998;
- 11bV. T. Mathad, S. Venkataraman, R. L. Kumari, M. Arunagiri, C. R. Reddy, M. Ramakrishna, K. S. Reddy, N. Srinivasan, K. Srinivas, Org. Process Res. Dev. 2005, 9, 314;
- 11cH. Rhee, S. Park, D. Park, J. Ko, K. D. Castro, Org. Process Res. Dev. 2007, 11, 918.
- 12
- 12aV. Nair, Synth. Commun. 1987, 17, 723–727;
- 12bJ. M. Lee, T. H. Tseng, Y. J. Lee, Synthesis 2001, 2247–2254;
- 12cF. Roelens, K. Huvaere, W. Dhooge, M. Van Cleemput, F. Comhaire, D. DeKeukeleire, Eur. J. Med. Chem. 2005, 40, 1042–1051;
- 12dK. Li, L. N. Foresee, J. A. Tunge, J. Org. Chem. 2005, 70, 2881–2883;
- 12eE. Fillion, A. M. Dumas, B. A. Kuropatwa, N. R. Malhotra, T. C. Sitler, J. Org. Chem. 2006, 71, 409–412;
- 12fC. E. Rodrigues-Santos, A. Echevarria, Tetrahedron Lett. 2007, 48, 4505–4508;
- 12gJ. Sun, W. X. Ding, X. P. Hong, K. Y. Zhang, Y. Zou, Chem. Nat. Compd. 2012, 48, 16–22;
- 12hP. Niharika, B. V. Ramulu, G. Satyanarayana, Org. Biomol. Chem. 2014, 12, 4347–4360.
- 13
- 13aH. Kim, J. Yun, Adv. Synth. Catal. 2010, 352, 1881–1885;
- 13bF. Ulgheri, M. Marchetti, O. Piccolo, J. Org. Chem. 2007, 72, 6056–6059.
- 14Rh-catalyzed asymmetric 1,4-addition:
- 14aC. Defieber, J. F. Paquin, S. Serna, E. M. Carreira, Org. Lett. 2004, 6, 3873–3876;
- 14bG. Chen, N. Tokunaga, T. Hayashi, Org. Lett. 2005, 7, 2285–2288;
- 14cT. Korenaga, R. Maenishi, K. Osaki, T. Sakai, Heterocycles 2010, 80, 157–162;
- 14dY. Luo, A. J. Carnell, Angew. Chem. Int. Ed. 2010, 49, 2750–2754; Angew. Chem. 2010, 122, 2810–2814;
- 14eJ. C. Allen, G. Kociok-Köhn, C. G. Frost, Org. Biomol. Chem. 2012, 10, 32–35;
- 14fT. Mino, K. Miura, H. Taguchi, K. Watanabe, M. Sakamoto, Tetrahedron: Asymmetry 2015, 26, 1065–1068.
- 15X.-H. Li, P. Fang, D. Chen, X.-L. Hou, Org. Chem. Front. 2014, 1, 969–973.
- 16L. Caruana, M. Mondatori, V. Corti, S. Morales, A. Mazzanti, M. Fochi, L. Bernardi, Chem. Eur. J. 2015, 21, 6037–6041.
- 17
- 17aT. Nishikata, Y. Yamamoto, N. Miyaura, Adv. Synth. Catal. 2007, 349, 1759–1764;
- 17bG. Yue, K. Lei, H. Hirao, J. S. Zhou, Angew. Chem. Int. Ed. 2015, 54, 6531–6535; Angew. Chem. 2015, 127, 6631–6635;
- 17cI. Ibrahem, G. Ma, S. Afewerki, A. Córdova, Angew. Chem. Int. Ed. 2013, 52, 878–882; Angew. Chem. 2013, 125, 912–916;
- 17dG. Li, Z. Li, Q. Gu, S. You, Org. Lett. 2017, 19, 1318–1321.
- 18
- 18aC. Qian, W. Tang, Org. Lett. 2020, 22, 4483–4488;
- 18bG. Liu, X. Liu, Z. Cai, G. Jiao, G. Xu, W. Tang, Angew. Chem. Int. Ed. 2013, 52, 4235–4238; Angew. Chem. 2013, 125, 4329–4332;
- 18cK. Li, M. Nie, W. Tang, Green Synth. Catal. 2020, 1, 173–177;
- 18dG. Xu, C. H. Senanayake, W. Tang, Acc. Chem. Res. 2019, 52, 1101–1112.
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