Asymmetric synthesis of allylic secondary alcohols: Anewgeneral approach for the preparation of α-amino acids

Tetrahedron

Volumn 66, Issue 29, 2010, Pages 5349-5356

  Drummond, Lorna J ^a   Sutherland, Andrew ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

Amino acids; Asymmetric reduction; Cross metathesis; Overman rearrangement

Indexed keywords

ALLYL ALCOHOL; ALPHA AMINO ACID; HYDROCINNAMIC ACID; KETONE DERIVATIVE; OXAZABOROLIDINE DERIVATIVE; RUTHENIUM; TRICHLOROACETIMIDIC ACID;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CROSS COUPLING REACTION; PRIORITY JOURNAL; THERMAL ANALYSIS;

EID: 77954310587     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.05.066     Document Type: Article

References (68)

1. (a)Barrett, G.C.Chemistry and Biochemistry of Amino Acids; Chapman and Hall: London 1985;
2. (b)Greenstein, J.P.; Winitz, M.Chemistry of the Amino Acids; Krieger: Malabar, FL, 1984; Vols.1-3.
3. Herbert, R.A.The Biosynthesis of Secondary Metabolites; Chapman and Hall: London, 1981.
4. (a)Izumi, Y.; Chibata, I.; Itoh, T.Angew.Chem., Int.Ed.Engl.1978, 17, 176-183;
5. (b)Jurczak, J.; Golebiowski, A.Chem.Rev.1989, 89, 149-164.
6. (a)Kelly, N.M.; Sutherland, A.; Willis, C.L.Nat.Prod.Rep.1997, 14, 205-220;
7. (b)Sutherland, A.; Willis, C.L.Nat.Prod.Rep.2000, 17, 621-631;
8. (c)Dougherty, D.A.Curr.Opin.Chem.Biol.2000, 4, 645-652;
9. (d)Wang, L.; Brock, A.; Herberich, B.; Schultz, P.G.Science 2001, 292, 498-500;
10. (e)Ohfune, Y.; Shinada, T.Eur.J.Org.Chem.2005, 5127-5143;
11. (f)Vogt, H.; Br€ase, S.Org.Biomol.Chem.2007, 5, 406-430;
12. (g)Smits, R.; Cadicamo, C.D.; Burger, K.; Koksch, B.Chem.Soc.Rev.2008, 37, 1727-1739;
13. (h)Mortensen, M.; Husmann, R.; Veri, E.; Bolm, C.Chem.Soc.Rev.2009, 38, 1002-1010;
14. (i)Katrizky, A.R.; Narindoshvili, T.Org.Biomol.Chem.2009, 7, 627-634;
15. (j)Gonçalves, M.S.T.Chem.Rev.2009, 109, 190-212;
16. (k)Fowler, L.S.; Ellis, D.; Sutherland, A.Org.Biomol.Chem.2009, 7, 4309-4316.
17. (a)Gibson, S.E.; Guillo, N.; Tozer, M.J.Tetrahedron 1999, 55, 585-615;
18. (b)Hruby, V.J.; Soloshonok, V.A.Tetrahedron Symposia-in-Print Number 88 Tetrahedron 2001, 57, ix
19. (a)For example, see: Williams, R.M.Synthesis of Optically Active a-Amino Acids; Pergamon: Oxford, 1989
20. (b)Duthaler, R.O.Tetrahedron 1994, 50, 1539-1650;
21. (c)Cativiela, C.; Diaz-de-Villegas, M.D.Tetrahedron: Asymmetry 1998, 9, 3517-3599;
22. (d)Cativiela, C.; Diaz-de-Villegas, M.D.Tetrahedron: Asymmetry 2000, 11, 645-732;
23. (e)Cativiela, C.; Diaz-de-Villegas, M.D.Tetrahedron: Asymmetry 2007, 18, 569-623;
24. (f)Cativiela, C.; Ordóñez, M.Tetrahedron: Asymmetry 2009, 20, 1-63;
25. (g)Amino Acids, Peptides and Proteins in Organic Chemistry; Hughes, A.B., Ed.; Wiley-VCH: Weinheim, 2009; Vol.1;
26. (h)Solo-shonok, V.A.; Ueki, H.; Ellis, T.K.Synlett 2009, 704-715;
27. (i)Michaux, J.; Niel, G.; Campagne, J.-M.Chem.Soc.Rev.2009, 38, 2093-2116.
28. Overman, L.E.; Carpenter, N.E.In Organic Reactions; Overman, L.E., Ed.; Wiley: Hoboken, NJ, 2005; Vol.66, pp 1-107; and references therein.8.
29. (a)Vyas, D.M.; Chiang, Y.; Doyle, T.W.Tetrahedron Lett.1984, 25, 487-490;
30. (b)Savage, I.; Thomas, E.J.J.Chem.Soc., Chem.Commun.1989, 717-719;
31. (c)Mehmandoust, M.; Petit, Y.; Larchevêque, M.Tetrahedron Lett.1992, 33, 4313-4316;
32. (d)Gonda, J.; Helland, A.-C.; Ernst, B.; Bellus, D.Synthesis 1993, 729-733;
33. (e)Marshall, J.A.; Garofalo, A.W.J.Org.Chem.1993, 58, 3675-3680;
34. (f)Estieu, K.; Ollivier, J.; Salaün, J.Tetrahedron Lett.1995, 36, 2975-2978;
35. (g)Imogaï, H.; Petit, Y.; Larchevêque, M.Tetrahedron Lett.1996, 37, 2573-2576;
36. (h)Chen, Y.K.; Lurain, A.E.; Walsh, P.J.J.Am.Chem.Soc.2002, 12225-12231;
37. (i)Anderson, C.E.; Overman, L.E.J.Am.Chem.Soc.2003, 12412-12413;
38. (j)Jamieson, A.G.; Sutherland, A.; Willis, C.L.Org.Biomol.Chem.2004, 2, 808-809;
39. (k)Fanning, K.N.; Jamieson, A.G.; Sutherland, A.Org.Biomol.Chem.2005, 3, 3749-3756;
40. (l)Swift, M.D.; Sutherland, A.Org.Biomol.Chem.2006, 4, 3889-3891;
41. (m)Swift, M.D.; Sutherland, A.Tetrahedron Lett.2007, 48, 3771-3773;
42. (n)Swift, M.D.; Sutherland, A.Tetrahedron 2008, 64, 9521-9527
43. CBS represents the initials of the researchers who discovered the oxazabor-olidine reagents, namely, Corey, Bakshi and Shibata:
44. (a) Corey, E.J.; Bakshi, R.K.; Shibata, S.J.Am.Chem.Soc.1987, 109, 5551-5553;
45. (b)Corey, E.J.; Bakshi, R.K.; Shibata, S.; Chen, C.-P.; Singh, V.K.J.Am.Chem.Soc.1987, 109, 7925-7926.
46. Martín, R.; Romea, P.; Tey, C.; Urpí, F.; Vilarrasa, J.Synlett 1997, 1414-1416.
47. (a)Scholl, S.; Ding, S.; Lee, C.W.; Grubbs, R.H.Org.Lett.1999, 1, 953-956;
48. (b)Sanford, M.S.; Love, J.A.; Grubbs, R.H.J.Am.Chem.Soc.2001, 123, 6543-6554.
49. (a)Chatterjee, A.K.; Choi, T.-L.; Sanders, D.P.; Grubbs, R.H.J.Am.Chem.Soc.2003, 125, 11360-11370;
50. (b)Paul, T.; Sirasani, G.; Andrade, R.B.Tetrahedron Lett.2008, 49, 3362-3367.
51. (a)Corey, E.J.; Helal, C.J.Angew.Chem., Int.Ed 1998, 37, 1986-2012
52. (b)Cho, B.T.Tetrahedron 2006, 62, 7621-7643.
53. The enantiomeric excess of compounds 10-13 was determined by chiral HPLC.Racemic standards were prepared by reduction of ketones 4, 5, 6 and 7 with sodium borohydride.
54. Hollis, T.K.; Overman, L.E.J.Organomet.Chem.1999, 576, 290-299.
55. Nishikawa, T.; Asai, M.; Ohyabu, N.; Isobe, M.J.Org.Chem.1998, 63, 188-192.
56. Carlsen, P.H.J.; Katsuki, T.; Martin, V.S.; Sharpless, K.B.J.Org.Chem.1981, 46, 3936-3938.
57. de Figueiredo, R.M.; Coudray, L.; Dubois, J.Org.Biomol.Chem.2007, 5, 3299-3309.
58. Jacob, M.; Roumestant, M.L.; Viallefont, P.; Martinez, J.Synlett 1997, 691-692.
59. Yasui, Y.; Tsuchida, S.; Miyabe, H.; Takemoto, Y.J.Org.Chem.2007, 72, 5898-5900.
60. Sugawara, Y.; Yamada, W.; Yoshida, S.; Ikeno, T.; Yamada, T.J.Am.Chem.Soc.2007, 129, 12902-12903.
61. Kato, M.; Kuwajima, I.Bull.Chem.Soc.Jpn.1984, 57, 827-830.
62. Tori, M.; Hashimoto, A.; Hirose, K.; Asakawa, Y.Phytochemistry 1995, 40, 1263-1264.
63. Kalivretenos, A.; Stille, J.K.; Hegedus, L.S.J.Org.Chem.1991, 56, 2883-2894.
64. Wipf, P.; Ribe, S.J.Org.Chem.1998, 63, 6454-6455.
65. Baldwin, J.E.; Spivey, A.C.; Schofield, C.J.; Sweeney, J.B.Tetrahedron 1993, 49, 6309-6330.
66. Corey, E.J.; Link, J.O.J.Am.Chem.Soc.1992, 114, 1906-1908.
67. Bull, S.D.; Davies, S.G.; O'Shea, M.D.J.Chem.Soc., Perkin Trans.1 1998, 3657-3658.
68. Yoshifuji, S.; Tanaka, K.-I.; Nitta, Y.Chem.Pharm.Bull.1987, 35, 2994-3001.