Intermolecular Phenolic Hydroxy Methylation Occurring between Chiral N,N′-Bis(2-hydroxyphenyl)-2,2-dimethyl-1,3-dioxolane-4,5-dicarbamide and Co-crystallized Methanol under Electron Impact Ionization Conditions
Jia-Xi Xu
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Department of Chemical Biology. College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
Search for more papers by this authorPeng Jiao
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Department of Chemical Biology. College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
Search for more papers by this authorZheng He
State Key Laboratory of Rare Earth, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
Search for more papers by this authorQi-Han Zhang
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Department of Chemical Biology. College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
Search for more papers by this authorChun-Hua Yan
State Key Laboratory of Rare Earth, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
Search for more papers by this authorJia-Xi Xu
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Department of Chemical Biology. College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
Search for more papers by this authorPeng Jiao
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Department of Chemical Biology. College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
Search for more papers by this authorZheng He
State Key Laboratory of Rare Earth, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
Search for more papers by this authorQi-Han Zhang
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Department of Chemical Biology. College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
Search for more papers by this authorChun-Hua Yan
State Key Laboratory of Rare Earth, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
Search for more papers by this authorAbstract
An intermolecular phenolic hydroxy methylation occurring between chiral N,N′-bis(2-hydroxyphenyl)-2,2-dimethyl-1,3-dioxolane-4,5dicarbamide and co-crystallized methanol under electron impact ionization conditions was observed. The result was confirmed by X-ray diffraction structural analysis of a co-crystalline of (R,R)-enantiomer and methanol.
References
- 1 Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem, Int. Ed. Engl. 1995, 34, 2386.
- 2 Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104.
- 3 Trost, B. M.; Hildbrand, S.; Dogra, K. J. Am Chem Soc. 1999, 121, 10416.
- 4 Belda, O.; Kaiser, N. F.; Bremberg, U.; Larhed, M.; Hallberg, A.; Moberg, C. J. Org. Chem. 2000, 65, 5868.
- 5 Malkov, A. V.; Spoor, P.; Vmader, V.; Kocovsky, P. Tetrahedron Lett. 2001, 42, 509.
- 6 Trost, B. M.; Oslob, J. D. J. Am Chem Soc. 1999, 121, 3057.
- 7 Adolfsson, H.; Moberg, C. Tenahedron: Asymmetry 1995, 6, 2023.
- 8 Quirmback, M.; Holz, J.; Tararov, V. I.; Borner, A. Tetrahedron 2000, 56, 775.
- 9 Amaud, N.; Cazaux, L.; Times, P.; Picard, C. Synlett 1994, 553.
- 10 Chang, S. K.; Engen, D. V.; Fan, E.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 7640.
- 11 Kluger, R.; Two, B. J. Am Chem Soc. 1993, 115, 2089.
- 12 Ma, G.; Jung, Y. S.; Chung, D. S.; Hong, J. I. Tetrahedron Lon. 1999, 40, 531.
- 13 Lessmann, J. J.; Horrocks, W. D. Jr. Inorg. Chem. 2000, 39, 3114.
- 14 Jiao, P.; Xu, J. X.; Zhang, Q. H.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 3081.
- 15 Xu, J. X.; Jiao, P.; Deng, D. Y.; Zhang, Q. H.; Tsang, C. W.; Chan, A. S. C. Rapid Commun. Mass Spectrom. 2002, 16, 1174.
- 16 Chen, Y. Z.; Li, H.; Hua, S. M.; Chen, N. Y.; Zhao, F. Z.; Li, H. Q. J. Chin Mass Spectrom Soc. 1988, 9, 7.
- 17 Li, H.; Chen, Y. Z.; Hua, S. M.; Chen, N. Y.; Chen, N.; Zhao, F. Z. Org. Mass Spectmm. 1986, 21, 726.
- 18 Xu, J. X.; Zuo, G. Rapid Commun. Mass Spectrom. 2003, 17, 1651.
- 19 Xu, J. X.; Zhang, X. Y.; Jin, S. Chin. J. Chem. 2000, 18, 368.
- 20
Xu, J. X.;
Lan, R. X.;
Jin, S.
Rapid Commun. Mass Spectrom.
1999,
13, 1511.
10.1002/(SICI)1097-0231(19990730)13:14<1511::AID-RCM677>3.0.CO;2-5 CAS PubMed Web of Science® Google Scholar
