Asymmetric induction in Darzens condensation by means of (–)-8-phenylmenthyl and (–)-menthyl auxiliaries

Abstract

Asymmetric Darzens condensation of benzaldehyde and various ketones has been investigated. The condensation of acetophenone, propiophenone and symmetric ketones with (–)-8-phenylmenthyl halogenoacetates 3a,b afforded the corresponding glycidic esters cis-12, cis-13 and 15–19 in 77–96% de, respectively, as the major products. Aza-Darzens condensation between N-benzylideneaniline and 3a occurred to give the trans-aziridine 21 as the major isomer in >85% de. The stereochemistry of the major diastereoisomers of cis-12 and 18 was confirmed by their conversion into the known optically active diols 22 and 24. The configuration of the major product of cis-12 was determined to be 2R,3R and that of 18 to be 2R. The geometric and disastereofacial selectivities were understandable in terms of the open-chain or non-chelated antiperiplanar transition state model in the initial aldol-type reaction.

References

1. (a) M. Bartok and K. L. Lang, in The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and Their Sulphur Analoges, Supplement E, S. Patai, ed., John Wiley, New York, 1980, vol. 2, p. 609; (b) J. M. Chong and K. B. Sharpless, J. Org. Chem., 1985, 50, 1560; (c) C. H. Behrens and K. B. Sharpless, J. Org. Chem., 1985, 50, 5696; (d) L. Deng and E. N. Jacobsen, J. Org. Chem., 1992, 57, 4320; (e) D.-M. Gou, Y.-C. Liu and C.-S. Chen, J. Org. Chem., 1993, 58, 1287; (f) C. Bonini and G. Righi, Synthesis, 1994, 225.
2. T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc., 1980, 102, 5974; R. A. Johnson and K. B. Sharpless, in Comprehensive Organic Synthesis, B. M. Trost, ed., Pergamon Press, Oxford, 1991, vol. 7, ch. 3.2; C. H. Behrens and K. B. Sharpless, Aldrichimica Acta, 1983, 16, 67; A. Pfenninger, Synthesis, 1986, 89.
3. (a) C. Clark, P. Hermans, O. Meth-Cohn, C. Moore, H. C. Taljaard and G. van Vuuren, J. Chem. Soc., Chem. Commun., 1986, 1378; (b) O. Meth-Cohn, C. Moore and H. C. Taljaard, J. Chem. Soc., Perkin Trans. 1, 1988, 2663; (c) T. Yoshimitsu and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1994, 2197; (d) D. Enders, J. Zhu and G. Raabe, Angew. Chem., Int. Ed. Engl., 1996, 35, 1725.
4. M. S. Newman and B. J. Magerlein, in Organic Reactions, John Wiley, 1945, vol. 5, p. 413; M. Ballester, Chem. Rev., 1955, 55, 283; G. Berti, Top. Stereochem., 1973, 7, 93; J. March, in Advanced Organic Chemistry, 3rd edn., Wiley, New York, 1985, p. 843 and references therein.
5. H. E. Zimmerman and L. Ahramjian, J. Am. Chem. Soc., 1960, 82, 5459.
6. J. D. Morrison and H. S. Mosher, in Asymmetric Organic Reactions, Prentice-Hall, N. J., 1971; p. 152; H. Dahn and L. Loewe, Chimia, 1957, 11, 98.
7. Diastereoselective Darzens type condensation between a bromoethyloxazoline (bromopropionate equivalent) with acetone has been reported, see J. R. Liddell and C. G. Whiteley, S. Afr. J. Chem., 1991, 44, 35.
8. M.-C. Roux-Schmitt, J. Seyden-Penne and S. Wolfe, Tetrahedron, 1972, 28, 4965.
9. R. K. Bansal and M. K. Sethi, Bull. Chem. Soc. Jpn., 1980, 53, 1197.
10. T. Mukaiyama, T. Haga and N. Iwasawa, Chem. Lett., 1982, 1601; A. Abdel-Magid, L. N. Pridgen, D. S. Eggleston and I. Lantos, J. Am. Chem. Soc., 1986, 108, 4595; C. Baldoli, P. D, Buttero and S. Maiorana, Tetrahedron, 1990, 46, 7823; E. J. Corey and S. Choi, Tetrahedron Lett., 1991, 32, 2857; L. N. Pridgen, A. F. Abdel-Magid, I. Lantos, S. Shilcrat and D. S. Eggleston, J. Org. Chem., 1993, 58, 5107; T. Takahashi, M. Muraoka, M. Capo and K. Koga, Chem. Pharm. Bull., 1995, 43, 1821.
11. (a) For a review: J. K. Whitesell, Chem. Rev., 1992, 92, 953; G. B. Jones and B. J. Chapman, Synthesis, 1995, 475; (b) S. E. Denmark, M. E. Schnute and C. B. W. Senanayake, J. Org. Chem., 1993, 58, 1859; N. Shida, C. Kabuto, T. Niwa, T. Ebata and Y. Yamamoto, J. Org. Chem., 1994, 59, 4068; K. Ohkata, K. Miyamoto, S. Matsumura and K.-y. Akiba, Tetrahedron Lett., 1993, 34, 6575; K. Ohkata, T. Kubo, K. Miyamoto, M. Ono, J. Yamamoto and K.-y. Akiba, Heterocycles, 1994, 38, 1483 Asymmetric Darzens reaction of p-anisaldehyde: J. T. Palmer, Chem. Abstr., 1990, 112, 198431p , (Eur. Pat. Appl. EP 342,904).
12. E. J. Corey, K. B. Becker and R. K. Varma, J. Am. Chem. Soc., 1972, 94, 8616; J. F. Maddaluno, N. Gresh and C. Giessner-Prettre, J. Org. Chem., 1994, 59, 793; B. de Pascual-Teresa, J. Gonzalez, A. Asensio and K. N. Houk, J. Am. Chem. Soc., 1995, 117, 4347.
13. (a) E. J. Corey and R. T. Peterson, Tetrahedron Lett., 1985, 26, 5025; (b) M. Ihara, M. Takahashi, N. Taniguchi, K. Yasui, K. Fukumoto and T. Kametani, J. Chem. Soc., Perkin Trans. 1, 1989, 897; (c) M. Ihara, M. Takahashi, N. Taniguchi, K. Yasui, H. Niitsuma and K. Fukumoto, J. Chem. Soc., Perkin Trans. 1, 1991, 525; (d) D. Basavaiah and T. K. Bharathi, Tetrahedron Lett., 1991, 32, 3417; (e) C. S. Swindell and M. Tao, J. Org. Chem., 1993, 58, 5889; (f) C. Alvarez-Ibarra, A. G. Csákÿ, R. Maroto and M. L. Quiroga, J. Org. Chem., 1995, 60, 7934.
14. For a preliminary report, see: K. Ohkata, J. Kimura, Y. Shinohara, R. Takagi and Y. Hiraga, Chem. Commun., 1996, 2411.
15. (a) K. B. Hansen, N. S. Finney and E. N. Jacobsen, Angew. Chem., Int. Ed. Engl., 1995, 34, 676; (b) A. A. Cantrill, L. D. Hall, A. N. Jarvis, H. M. I. Osborn, J. Raphy and J. B. Sweeney, Chem. Commun., 1996, 2631.
16. T. Hosokawa, T. Yagi, Y. Ataka and S.-I. Murahashi, Bull. Chem. Soc. Jpn., 1988, 61, 3380; S. Mitsui, S. Imaizumi, Y. Senda and K. Konno, Chem. Ind. (London), 1964, 233.
17. J. S. Sabol and R. J. Cregge, Tetrahedron Lett., 1990, 31, 27; P. S. Vankar, I. Bhattacharya and Y. D. Vankar, Tetrahedron: Asymmetry, 1996, 7, 1683.
18. K.-Y. Ko, W. J. Frazee and E. L. Eliel, Tetrahedron, 1984, 40, 1333.
19. R. F. Borch, Tetrahedron Lett., 1972, 3761.
20. Y. Yamamoto and K. Maruyama, Tetrahedron Lett., 1980, 21, 4607; S. Murata, M. Suzuki and R. Noyori, J. Am. Chem. Soc., 1980, 102, 3248; Y. Yamamoto, H. Yatagai, Y. Naruta and K. Maruyama, J. Am. Chem. Soc., 1980, 102, 7107; H. Danda, M. M. Hansen and C. H. Heathcock, J. Org. Chem., 1990, 55, 173; M. A. Walker and C. H. Heathcock, J. Org. Chem., 1991, 56, 5747.
21. Y. Li, M. N. Paddon-Row and K. N. Houk, J. Am. Chem. Soc., 1988, 110, 3684; Y. Li, M. N. Paddon-Row and K. N. Houk, J. Org. Chem., 1990, 55, 481.
22. H. O. House and B. M. Trost, J. Org. Chem., 1965, 30, 1341; D. W. Moreland and W. G. Dauben, J. Am. Chem. Soc., 1985, 107, 2264.
23. K. Sisido, O. Nakanisi and H. Nozaki, J. Org. Chem., 1961, 26, 4878; H. Yanagisawa, K. Fujimoto, Y. Shimoji, T. Kanazaki, K. Mizutari, H. Nishino, H. Shiga and H. Koike, Chem. Pharm. Bull., 1992, 40, 2055.
24. J. Jurczak and A. Zamojski, Rocz. Chem., 1970, 44, 2257; R. Grigg, J. Markandu, T. Perrior, S. Surendrakumar and W. J. Warnock, Tetrahedron, 1992, 48, 6929.
25. O. Ort, Org. Synth., 1985, 65, 203.
26. J. K. Whitesell, A. Bhattacharya, C. M. Buchanan, H. H. Chen, D. Deyo, D. James, C.-L. Liu and M. A. Minton, Tetrahedron, 1986, 42, 2993; A. Solladie-Cavallo and N. Khiar, Tetrahedron Lett., 1988, 29, 2189.
27. T. Inokuchi, S. Kusumoto, S. Matsumoto, H. Okada and S. Torii, Chem. Lett., 1991, 2009.
28. K. Kogure, K. Nakagawa and H. Fukawa, Agric. Biol. Chem., 1976, 40, 1547.
29. A. Mosandl, Z. Lebensm.-Unters. Forsch., 1983, 177, 129.