Construction of α-phosphonolactams via rhodium (II)-catalyzed intramolecular CH insertion reactions†
Yoshiharu Okada
Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu 804, Japan
Search for more papers by this authorCorresponding Author
Toru Minami
Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu 804, Japan
Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu 804, JapanSearch for more papers by this authorMasahiro Miyamoto
Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu 804, Japan
Search for more papers by this authorTsuneyuki Otaguro
Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu 804, Japan
Search for more papers by this authorSumiko Sawasaki
Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu 804, Japan
Search for more papers by this authorJunji Ichikawa
Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu 804, Japan
Search for more papers by this authorYoshiharu Okada
Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu 804, Japan
Search for more papers by this authorCorresponding Author
Toru Minami
Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu 804, Japan
Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu 804, JapanSearch for more papers by this authorMasahiro Miyamoto
Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu 804, Japan
Search for more papers by this authorTsuneyuki Otaguro
Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu 804, Japan
Search for more papers by this authorSumiko Sawasaki
Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu 804, Japan
Search for more papers by this authorJunji Ichikawa
Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu 804, Japan
Search for more papers by this authorDedicated to Prof. Shigeru Oae on the occasion of his seventy-fifth birthday.
Abstract
The Rh(II)-catalyzed intramolecular CH insertion reactions of N,N-dialkyl-α-diazo-α-(diethylphosphono)acetamides 2a,f–j in CHCl3 or ClCH2CH2Cl were found to give monocyclic and bicyclic α-phosphono-β-lactams, 3a and 3f–j, in 43–67% yields via regiospecific α-CH insertion of the N-alkyl groups. Similar treatment of N-benzyl-N-isopropyl-α-diazo-α-(diethylphosphono)acetamide (2b) and the corresponding N-isobutyl-N-methylacetamide 2d in ClCH2CH2Cl afforded mixtures of β-lactams 3b (35%) and and 3b′ (16%), β-lactam 3d (47%), and γ-lactam 4d (10%), respectively, each of which is formed by the competitive CH insertion reaction between benzylic and isopropyl α-CH bonds and between methyl α-CH and methine β-CH bonds, respectively. For the formation of β-lactams, the selectivity in the rhodium-mediated CH insertion in ClCH2CH2Cl follows the order methyl > methine > benzylic α-CH bond on N-substituents. The N,N-dibutyl-α-diazo homologue 2c and Nα[α-diazo-α-(diethylphosphono)acetyl]-2-methylindoline (2k) exclusively produced γ-lactams 4c (67%) and 4k (81%) via insertion into the methylene β-CH and methyl β-CH bonds. tert-Butyl N-[α-diazo-α-(dibenzylphosphono)acetyl]-piperidine-2-carboxylate (2m) on similar treatment, followed by deprotection of the benzyl ester afforded the 7-phosphono carbacepham 6 in 32% overall yield. Similar Rh(II)-catalyzed cyclization of N-methyl-N[4-benzyloxy-α-(diethylphosphono)-phenyl(diethyl-phosphono)methyl]-α-diazo-acetamide (2n) led to 1-[4′-benzylphenyl(diethylphosphono)methyl] -3-(diethyl-phosphono)azetidin-2-one (3n) in 78% yicld. The phosphono group at C-7 of 3f was converted into the acetylamino group via a four-step reaction. Application of chiral rhodium(II) carboxylates 12a–c to the insertion reactions of 2b,c produced α-phosphono-β-and γ-lactams, 3b and 4c, in 6–24% ee and 25–29% ee, respectively.
References
- 1(a)
For reviews of rhodium(II)-catalyzed reactions, see
S. D. Burke,
P. A. Grieco,
Org. React.,
26,
1979,
361;
(b)
M. P. Doyle,
Chem. Rev.,
86,
1986,
919;
(c)
G. Maas,
Topics Curr. Chem.,
137,
1987,
75;
(d)
J. Adams,
D. M. Spero,
Tetrahedron,
47,
1991,
1765;
(e)
D. F. Taber:
Carbon–Carbon Bond Formation by CH Insertion,
in B. M. Trost,
I. Fleming (eds):
Comprehensive Organic Synthesis,
Pergamon Press, Oxford,
vol. 3,
pp. 1045–1062
(1991).
10.1016/B978-0-08-052349-1.00089-5 Google Scholar
- 2(a) J. Adams, M.-A. Poupart, L. Grenier, C. Schaller, N. Ouimet, R. Frenette, Tetrahedron Lett., 30, 1989, 1749; (b) J. Adams, M.-A. Poupart, L. Grenier, Tetrahedron Lett., 30, 1989, 1753; (c) H. R. Sonawane, N. S. Bellur, J. R. Ahuja, D. G. Kulkarni, J. Org. Chem., 56, 1991, 1434; (d) P. Padwa, D. J. Austin, S. F. Hornbuckle, M. A. Semones, J. Am. Chem. Soc., 114, 1992, 1874.
- 3(a) D. F. Taber, E. H. Petty, J. Org. Chem., 47, 1982, 4808; (b) D. F. Taber, J. L. Schuchardt, J. Am. Chem. Soc., 107, 1985, 5289; (c) D. F. Taber, R. E. Ruckle, Jr., Tetrahedron Lett., 26, 1985, 3059; (d) D. F. Taber, R. E. Ruckle, Jr., J. Am. Chem. Soc., 108, 1986, 7686; (e) D. F. Taber, J. L. Schuchardt, Tetrahedron, 43, 1987, 5677; (f) E. Lee, K. W. Jung, Y. S. Kim, Tetrahedron Lett., 31, 1990, 1023; (g) S. Hashimoto, N. Watanabe, S. Ikegami, Tetrahedron Lett., 33, 1992, 2709; (h) M. P. Doyle, L. J. Westrum, W. N. E. Wolthuis, M. M. See, W. P. Boone, V. Bagheri, M. M. Pearson, J. Am. Chem. Soc., 115, 1993, 958.
- 4 H. J. Monteiro, Tetrahedron Lett., 28, 1987, 3459.
- 5(a) B. Corbel, D. Hernot, J.-P. Haelters, G. Sturtz, Tetrahedron Lett., 28, 1987, 6605; (b) M. Mikolajczyk, R. Zurawinski, P. Kielbasinski, Tetrahedron Lett., 30, 1989, 1143.
- 6(a) M. P. Doyle, M. S. Shanklin, S.-M. Oon, H. Q. Pho, F. R. van der Heide, W. R. Veal, J. Org. Chem., 53, 1988, 3384; (b) M. P. Doyle, J. Taunton, H. Q. Pho, Tetrahedron Lett., 30, 1989, 5397; (c) M. P. Doyle, R. J. Pieters, J. Taunton, H. Q. Pho, A. Padwa, D. L. Hertzog, L. Precedo, J. Org. Chem., 56, 1991, 820.
- 7 J. Motoyoshiya, K. Hirata, Chem. Lett., 1988, 211.
- 8 T. Minami, M. Kamitamari, T. Utsunomiya, T. Tanaka, J. Ichikawa, Bull. Chem. Soc. Jpn., 66, 1993, 1496.
- 9(a) T. Minami, Y. Kitajima, T. Chikugo, Chem. Lett., 1986, 1229; (b) T. Minami, K. Hirakawa, S. Koyanagi, S. Nakamura, M. Yamaguchi, J. Chem. Soc., Perkin Trans., 1, 1990, 2385; (c) T. Minami, Y. Matsumoto, S. Nakamura, S. Koyanagi, M. Yamaguchi, J. Org. Chem., 57, 1992, 167.
- 10 M. Regitz, J. Hocker, A. Liedhegener: Organic Synthesis, Coll. V, Wiley, New York, p. 197 (1973).
- 11(a) The trans and cis coupling constants for hydrogens on β-lactam ring are in the range of 2.2–2.8 and 4.9–5.9 Hz, respectively. See H. B. Kagan, J. J. Basselier, J. L. Luche, Tetrahedron Lett., 1964, 941; (b) K. D. Barrow, T. M. Spotswood, Tetrahedron Lett., 1965, 3325.
- 12(a) J. D. Buynak, M. N. Rao, J. Org. Chem. 51, 1986, 1571; (b) T. Kametani, S.-D. Chu, A. Itoh, S. Maeda, T. Honda, J. Org. Chem., 53, 1988, 2683; (c) R. S. Miller, D. W. Hoard, R. A. Johnson, W. D. Luke, J. Org. Chem., 59, 1994, 3289.
- 13 W. Dürckheimer, J. Blumbach, R. Lattrell, K. H. Scheunemann, Angew. Chem. Int. Ed. Engl., 24, 1985, 180.
- 14(a) For the alternative synthesis of 3-methylene-β-lactams, see T. Minami, M. Ishida, T. Agawa, J. Chem. Soc., Chem. Commun., 1978, 12; (b) S. R. Fletcher, I. T. Kay, J. Chem. Soc., Chem. Commun., 1978, 903; (c) M. Ishida, T. Minami, T. Agawa, J. Org. Chem., 44, 1979, 2067; (d) M. Mori, K. Chiba, M. Okita, Y. Ban, J. Chem. Soc., Chem. Commun., 1979, 698; (e) R. M. Adlington, A. G. M. Barrett, P. Quayle, A. Walker, M. J. Betts, J. Chem. Soc., Chem. Commun., 1981, 404; (f) R. M. Adlington, A. G. M. Barrett, P. Quayle, A. Walker, M. J. Betts, J. Chem. Soc., Perkin Trans, 1, 1983, 605; (g) M. Mori, K. Chiba, M. Okita, I. Kayo, Y. Ban, Tetrahedron, 41, 1985, 375.
- 15 Chiba et al. have similarly reported the conversion of the 3-methylene-β-lactam containing the carboxylic acid esters side chain with aromatic ring into 3-amino-β-lactams: K. Chiba, M. Mori, Y. Ban, Tetrahedron, 41, 1985, 387.
- 16(a) For an enantioselective intramolecular CH insertion with chiral rhodium(II) carboxylates, see S. Hashimoto, N. Watanabe, S. Ikegami, Tetrahedron Lett., 31, 1990, 5173; (b) H. Brunner, K. Wutz, M. P. Doyle, Monatsh. Chem., 121, 1990, 755; (c) M. P. Doyle, A. van Oeveren, L. J. Westrum, M. N. Protopopova, T. W. Clayton, Jr., J. Am. Chem. Soc., 113, 1991, 8982; (d) M. P. Doyle, M. N. Protopopova, W. R. Winchester, K. L. Daniel, Tetrahedron Lett., 33, 1992, 7819; (e) M. P. Doyle, W. R. Winchester, J. A. A. Hoorn, V. Lynch, S. H. Simonsen, R. Ghosh, J. Am. Chem. Soc., 115, 1993, 9968. (f) For an enantioselective intramolecular CH insertion of the chiral substrates with rhodium(II) tetraacetate, see D. F. Taber, E. H. Petty, K. Raman, J. Am. Chem. Soc., 107, 1985, 196.
- 17(a) For a diastereoselective intramolecular CH insertion of chiral moiety containing substrates with rhodium(II) tetraacetate, see D. F. Taber, K. Raman, J. Am. Chem. Soc., 105, 1983, 5935; (b) D. F. Taber, K. Raman, M. D. Gaul, J. Org. Chem., 52, 1987, 28.
- 18(a) P. A. Agaskar, F. A. Cotton, L. R. Falvello, S. Han, J. Am. Chem. Soc., 108, 1986, 1214; (b) H. Brunner, H. Kluschanzoff, K. Wutz, Bull. Soc. Chim. Belg., 98, 1989, 63.
- 19 DPCProC oxide is the abbreviation of trans-2,3-bis(diphenylphosphinyl)-1-methyl-1-cyclopropane-carboxylic acid: Y. Okada, T. Minami, T. Yamamoto, J. Ichikawa, Chem. Lett., 1992, 547.
- 20(a) H. J. Callot, F. Metz, Tetrahedron, 41, 1985, 4495; (b) G. H. L. Nefkens, G. I. Tesser, R. J. F. Nivard, Recl. Trav. Chim. Pays-Bas, 79, 1960, 688.
- 21 SAPI91: Fan Hai-Fu: Structure Analysis Programs with Intelligent Control, Rigaku Corporation, Tokyo, Japan (1991).
- 22 DIRDIF92: P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, S. Garcia-Granda, R. O. Gould, J. M. M. Smits, C. Smykalla: The DIRDIF program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, Netherlands (1992).
- 23 Least-Squares: Function minimized:ΣW(|Fo| − |Fc|)2 \documentclass{article}\pagestyle{empty}\begin{document}$$ {\rm where}\,\,w = \frac{1}{{\sigma ^2 (Fo)}} = \frac{{4Fo}}{{\sigma ^2 (Fo^2)}}; $$\end{document} \documentclass{article}\pagestyle{empty}\begin{document}$$ \sigma ^2 (Fo^2) = \frac{{S^2 (C + R^2 B) + (pFo)^2 }}{{Lp^2 }}; $$\end{document} \documentclass{article}\pagestyle{empty}\begin{document}$$ \begin{array}{*{20}c} {S = \hbox{scan rate;}} \hfill \\ {C = \hbox{total intergrated peak count;}} \hfill \\ {R = \hbox{ratio of scan time to background counting time;}} \hfill \\ {B = \hbox{total background count};} \hfill \\ {Lp = \hbox{Lorentz - polazation factor};{\rm and}} \hfill \\ {p = p - {\rm factor}.} \hfill \\ \end{array} $$\end{document}
- 24 Standard deviation of an observation of unit weight: \documentclass{article}\pagestyle{empty}\begin{document}$$ \sqrt {\Sigma w(|Fo| - |Fc|)^2 /(No - Nv)} $$\end{document} where No = number of observations; and Nv = number of variables.
- 25 D. T. Cromer, J. T. Waber: International Tables for X-ray Crystallography, The Kynoch Press, Birmingham, England, vol. IV, Table 2.2 A (1974).
- 26 J. A. Ibers, W. C. Hamilton, Acta Crystallogr., 17, 1964, 781.
- 27 D. C. Creagh, W. J. McAuley: in A. J. C. Wilson (ed.): International Tables for Crystallography, Kluwer Academic Publishers, Boston, vol. C, pp. 219–222 (1992).
- 28 D. C. Creagh, J. H. Hubbell: in A. J. C. Wilson (ed.): International Tables for Crystallography, Kluwer Academic Publishers, Boston, vol. C, pp. 200–206 (1992).
- 29 teXsan: Crystal Structure Analysis Package, Molecular Structure Corporation, The Woodlands, TX, 77381 (1985 and 1992).
