Chiral oxime ethers in asymmetric synthesis. Part 4. Asymmetric synthesis of N-protected amines and β-amino acids by the addition of organometallic reagents to ROPHy/SOPHy-derived aldoximes

Abstract

Addition of organolithium or Grignard reagents to (R)- or (S )-O-(1-phenylbutyl)aldehyde oximes 1 in the presence of boron trifluoride–diethyl ether results in the formation of hydroxylamines 2 in good to excellent diastereoselectivity. Subsequent cleavage of the N–O bond with zinc–acetic acid–ultrasound, and carbamate formation, gives N-protected amines 3 in good enantiomeric purity (77–100% ee). When allylmagnesium bromide was used as the organometallic reagent, the resulting hydroxylamines were converted into β-amino acid derivatives 4 and γ-amino alcohols 5.

References

1. Part 3, C. J. Moody, P. T. Gallagher, A. P. Lightfoot and A. M. Z. Slawin, J. Org. Chem., 1999, 64, 4419.
2. For reviews, see: M. North, J. Chem. Soc., Perkin Trans. 1, 1999, 2209; 1998, 2959; Contemp. Org. Synth., 1997, 4, 326; 1996, 3, 323; 1995, 2, 269; A. Johansson, Contemp. Org. Synth., 1995, 2, 393.
3. For overviews, see: S. E. Denmark and O. J.-C. Nicaise, Chem. Commun., 1996, 999; D. Enders and U. Reinhold, Tetrahedron: Asymmetry, 1997, 8, 1895; R. Bloch, Chem. Rev., 1998, 98, 1407.
4. P. T. Gallagher, J. C. A. Hunt, A. P. Lightfoot and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1997, 2633.
5. C. J. Moody, A. P. Lightfoot and P. T. Gallagher, J. Org. Chem., 1997, 62, 746.
6. Preliminary communication; C. J. Moody and J. C. A. Hunt, Synlett, 1998, 733.
7. The authors have deposited atomic coordinates with the Cambridge Crystallographic Data Centre. The coordinates can be obtained on request from The Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK. CCDC reference number 207/360.
8. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902.
9. D. S. Brown, P. T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin and E. Swann, Tetrahedron, 1995, 51, 11473.
10. D. Enders and H. Kempen, Synlett, 1994, 969.
11. (a) Y. Son, C. Park, J. S. Koh, N. Choy, C. S. Lee, H. Choi, S. C. Kim and H. Yoon, Tetrahedron Lett., 1994, 35, 3745 We believe there is a typographical error in this paper; the (–)-amine is clearly drawn as (S), though it is tabulated as (R);; (b) U. B. Paulsen-Sörman, K.-H. Jönsson and B. G. A. Lindeke, J. Med. Chem., 1984, 27, 342.
12. For a recent approach to homoallylamines, see: S. Itsuno, K. Watanabe, T. Matsumoto, S. Kuroda, A. Yokoi and A. ElShehawy, J. Chem. Soc., Perkin Trans. 1, 1999, 2011.
13. For accounts of work on β-peptides, see: D. Seebach and J. L. Matthews, Chem. Commun., 1997, 2015; D. H. Appella, L. A. Christianson, I. L. Karle, D. R. Powell and S. H. Gellman, J. Am. Chem. Soc., 1996, 118, 13071; S. Krauthauser, L. A. Christianson, D. R. Powell and S. H. Gellman, J. Am. Chem. Soc., 1997, 119, 11719; S. Hanessian and H. Yang, Tetrahedron Lett., 1997, 38, 3155.
14. For reviews on the asymmetric synthesis of β-amino acids, see: D. C. Cole, Tetrahedron, 1994, 50, 9517; G. Cardillo and C. Tomasini, Chem. Soc. Rev., 1996, 25, 117; E. Juaristi, in Enantioselective Synthesis of β-Amino Acids, New York, 1997.
15. For recent examples of the Arndt–Eistert homologation of α-amino acids, see: J. Podlech and D. Seebach, Angew. Chem., Int. Ed. Engl., 1995, 34, 471 (Liebigs Ann., 1995, 1217); R. Caputo, E. Cassano, L. Longobardo and G. Palumbo, Tetrahedron, 1995, 51, 12337; D. Seebach, M. Overhand, F. N. M. Kuhnle, B. Martinoni, L. Oberer, U. Hommel and H. Widmer, Helv. Chim. Acta, 1996, 79, 913; C. Guibourdenche, D. Seebach and F. Natt, Helv. Chim. Acta, 1997, 80, 1; A. Leggio, A. Liguori, A. Procopio and G. Sindona, J. Chem. Soc., Perkin Trans. 1, 1997, 1969; R. E. Marti, K. H. Bleicher and K. W. Bair, Tetrahedron Lett., 1997, 38, 6145.
16. S. G. Davies and D. R. Fenwick, J. Chem. Soc., Chem. Commun., 1995, 1109; D. Enders, H. Wahl and W. Bettray, Angew. Chem., Int. Ed. Engl., 1995, 34, 455; D. Enders, J. Wiedemann and W. Bettray, Synlett, 1995, 369; M. P. Collis, D. C. R. Hockless and P. Perlmutter, Tetrahedron Lett., 1995, 36, 7133; L. Falborg and K. A. Jorgensen, J. Chem. Soc., Perkin Trans. 1, 1996, 2823; S. G. Davies, D. R. Fenwick and O. Ichihara, Tetrahedron: Asymmetry, 1997, 8, 3387; T. Ishikawa, K. Nagai, T. Kudoh and S. Saito, Synlett, 1998, 1291; M. P. Sibi, J. J. Shay, M. Liu and C. P. Jasperse, J. Am. chem. Soc., 1998, 120, 6615.
17. S. Laschat and H. Kunz, J. Org. Chem., 1991, 56, 5883; M. K. Mokhallalati, M. Wu and L. N. Pridgeon, Tetrahedron Lett., 1993, 34, 47; F. A. Davis, J. M. Szewczyk and R. E. Reddy, J. Org. Chem., 1996, 61, 2222; P. G. Cozzi, B. D. Simone and A. Umani-Ronchi, Tetrahedron Lett., 1996, 37, 1691; H. Kunz, A. Burgard and D. Schanzenbach, Angew. Chem., Int. Ed. Engl., 1997, 36, 386; D. Enders, J. Schankat and M. Klatt, Synlett, 1994, 795.
18. G. Righi, R. Dachille and C. Bonini, Tetrahedron Lett., 1996, 37, 6893; F. A. Davis, G. V. Reddy and C. H. Liang, Tetrahedron Lett., 1997, 38, 5139.
19. V. A. Soloshonok, N. A. Fokina, A. V. Rybakova, I. P. Shishkina, S. V. Galushko, A. E. Sorochinsky, V. P. Kukhar, M. V. Savchenko and V. K. Svedas, Tetrahedron: Asymmetry, 1995, 6, 1601; L. T. Kanerva, P. Csomos, O. Sundholm, G. Bernath and F. Fulop, Tetrahedron: Asymmetry, 1996, 7, 1705; V. A. Soloshonok, T. Ono and I. V. Soloshonok, J. Org. Chem., 1997, 62, 7538.
20. For other recent approaches, see ref. 14 and F. Beaulieu, J. Arora, U. Veith, N. J. Taylor, B. J. Chapell and V. Snieckus, J. Am. Chem. Soc., 1996, 118, 8727; J. F. Bower and J. M. J. Williams, Synlett, 1996, 685; M. Seki and K. Matsumoto, Tetrahedron Lett., 1996, 37, 3165; E. Juaristi, D. Quintana, M. Balderas and E. Garciaperez, Tetrahedron: Asymmetry, 1996, 7, 2233; F. J. Lakner, K. S. Chu, G. R. Negrete and J. P. Konopelski, Org. Synth., 1996, 73, 201; Y. S. Park and P. Beak, J. Org. Chem., 1997, 62, 1574; J. F. Bower, R. Jumnah, A. C. Williams and J. M. J. Williams, J. Chem. Soc., Perkin Trans. 1, 1997, 1411; M. FernandezSuarez, L. Munoz, R. Fernandez and R. Riguera, Tetrahedron: Asymmetry, 1997, 8, 1847; C. S. Dexter and R. F. W. Jackson, Chem. Commun., 1998, 75; D. Seebach, A. Boog and W. B. Schweizer, Eur. J. Org. Chem., 1999, 335; E. Arvanitis, H. Ernst, A. A. Ludwig, A. J. Robinson and P. B. Wyatt, J. Chem. Soc., Perkin Trans. 1, 1998, 521; Y. H. Jin and D. H. Kim, Synlett, 1998, 1189; E. Juaristi, M. Balderas and Y. RamirezQuiros, Tetrahedron: Asymmetry, 1998, 9, 3881; C. Agami, S. Cheramy, L. Dechoux and C. Kadouri-Puchot, Synlett, 1999, 727.
21. J. A. Marshall and A. W. Garofalo, J. Org. Chem., 1993, 58, 3675.
22. L. Crombie, D. Haigh, R. C. F. Jones and A. R. Mat-Zin, J. Chem. Soc., Perkin Trans. 1, 1993, 2047.
23. (a) For a review, see: A. G. Fallis and I. M. Brinza, Tetrahedron, 1997, 53, 17543; (b) H. Miyabe, C. Ushiro and T. Naito, Chem. Commun., 1997, 1789; (c) S. Kim, Y. Kim and K. S. Yoon, Tetrahedron Lett., 1997, 38, 2487; (d) H. Miyabe, R. Shibata, C. Ushiro and T. Naito, Tetrahedron Lett., 1998, 39, 631; (e) H. Miyabe, R. Shibata, M. Sangawa, C. Ushiro and T. Naito, Tetrahedron, 1998, 54, 11431; (f) H. Miyabe, K. Fujii and T. Naito, Org. Lett., 1999, 1, 569.
24. L. Börjesson, I. Csöregh and C. J. Welch, J. Org. Chem., 1995, 60, 2989.