Catalytic asymmetric synthesis of β-hydroxy-α-amino acid esters by direct aldol reaction of glycinate Schiff bases

Tetrahedron

Volumn 58, Issue 41, 2002, Pages 8289-8298

  Yoshikawa, Naoki ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

hydroxy amino acid; Benzophenone imine; Direct aldol reaction; Glycinate Schiff base; Glycine; Heterobimetallic asymmetric catalyst; Lanthanide; Vancomycin

Indexed keywords

ALDEHYDE DERIVATIVE; AMINO ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ETHER DERIVATIVE; SCHIFF BASE;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0037037987     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00979-1     Document Type: Article

References (76)

1. For a review, see: (a) Nicolaou K.C., Boddy C.N.C., Bräse S., Winssinger N. Angew. Chem., Int. Ed. 38:1999;2096-2152 (b) Boger D.L., Miyazaki S., Kim S.H., Wu J.H., Castle S.L., Loiseleur O., Jin Q. J. Am. Chem. Soc. 121:1999;10004-10011 (c) Boger D.L., Kim S.H., Mori Y., Weng J.-H., Rogel O., Castle S.L., McAtee J.J. J. Am. Chem. Soc. 123:2001;1862-1871 (d) Nicolaou K.C., Li H., Boddy C.N.C., Ramanjulu J.M., Yue T.-Y., Natarajan S., Chu X.-J., Bräse S., Rübsam F. Chem. Eur. J. 5:1999;2584-2601 (e) Nicolaou K.C., Boddy C.N.C., Li H., Koumbis A.E., Hughes R., Natarajan S., Jain N.F., Ramanjulu J.M., Bräse S., Solomon M.E. Chem. Eur. J. 5:1999;2602-2621 (f) Nicolaou K.C., Koumbis A.E., Takayanagi M., Natarajan S., Jain N.F., Bando T., Li H., Hughes R. Chem. Eur. J. 5:1999;2622-2647 (g) Nicolaou K.C., Mitchell H.J., Jain N.F., Bando T., Hughes R., Winssinger N., Natarajan S., Koumbis A.E. Chem. Eur. J. 5:1999;2648-2667 (h) Evans D.A., Wood M.R., Trotter B.W., Richardson T.I., Barrow J.C., Katz J.L. Angew. Chem., Int. Ed. 37:1998;2700-2704.
2. For a review, see: (a) Nicolaou K.C., Boddy C.N.C., Bräse S., Winssinger N. Angew. Chem., Int. Ed. 38:1999;2096-2152 (b) Boger D.L., Miyazaki S., Kim S.H., Wu J.H., Castle S.L., Loiseleur O., Jin Q. J. Am. Chem. Soc. 121:1999;10004-10011 (c) Boger D.L., Kim S.H., Mori Y., Weng J.-H., Rogel O., Castle S.L., McAtee J.J. J. Am. Chem. Soc. 123:2001;1862-1871 (d) Nicolaou K.C., Li H., Boddy C.N.C., Ramanjulu J.M., Yue T.-Y., Natarajan S., Chu X.-J., Bräse S., Rübsam F. Chem. Eur. J. 5:1999;2584-2601 (e) Nicolaou K.C., Boddy C.N.C., Li H., Koumbis A.E., Hughes R., Natarajan S., Jain N.F., Ramanjulu J.M., Bräse S., Solomon M.E. Chem. Eur. J. 5:1999;2602-2621 (f) Nicolaou K.C., Koumbis A.E., Takayanagi M., Natarajan S., Jain N.F., Bando T., Li H., Hughes R. Chem. Eur. J. 5:1999;2622-2647 (g) Nicolaou K.C., Mitchell H.J., Jain N.F., Bando T., Hughes R., Winssinger N., Natarajan S., Koumbis A.E. Chem. Eur. J. 5:1999;2648-2667 (h) Evans D.A., Wood M.R., Trotter B.W., Richardson T.I., Barrow J.C., Katz J.L. Angew. Chem., Int. Ed. 37:1998;2700-2704.
3. For a review, see: (a) Nicolaou K.C., Boddy C.N.C., Bräse S., Winssinger N. Angew. Chem., Int. Ed. 38:1999;2096-2152 (b) Boger D.L., Miyazaki S., Kim S.H., Wu J.H., Castle S.L., Loiseleur O., Jin Q. J. Am. Chem. Soc. 121:1999;10004-10011 (c) Boger D.L., Kim S.H., Mori Y., Weng J.-H., Rogel O., Castle S.L., McAtee J.J. J. Am. Chem. Soc. 123:2001;1862-1871 (d) Nicolaou K.C., Li H., Boddy C.N.C., Ramanjulu J.M., Yue T.-Y., Natarajan S., Chu X.-J., Bräse S., Rübsam F. Chem. Eur. J. 5:1999;2584-2601 (e) Nicolaou K.C., Boddy C.N.C., Li H., Koumbis A.E., Hughes R., Natarajan S., Jain N.F., Ramanjulu J.M., Bräse S., Solomon M.E. Chem. Eur. J. 5:1999;2602-2621 (f) Nicolaou K.C., Koumbis A.E., Takayanagi M., Natarajan S., Jain N.F., Bando T., Li H., Hughes R. Chem. Eur. J. 5:1999;2622-2647 (g) Nicolaou K.C., Mitchell H.J., Jain N.F., Bando T., Hughes R., Winssinger N., Natarajan S., Koumbis A.E. Chem. Eur. J. 5:1999;2648-2667 (h) Evans D.A., Wood M.R., Trotter B.W., Richardson T.I., Barrow J.C., Katz J.L. Angew. Chem., Int. Ed. 37:1998;2700-2704.
4. For a review, see: (a) Nicolaou K.C., Boddy C.N.C., Bräse S., Winssinger N. Angew. Chem., Int. Ed. 38:1999;2096-2152 (b) Boger D.L., Miyazaki S., Kim S.H., Wu J.H., Castle S.L., Loiseleur O., Jin Q. J. Am. Chem. Soc. 121:1999;10004-10011 (c) Boger D.L., Kim S.H., Mori Y., Weng J.-H., Rogel O., Castle S.L., McAtee J.J. J. Am. Chem. Soc. 123:2001;1862-1871 (d) Nicolaou K.C., Li H., Boddy C.N.C., Ramanjulu J.M., Yue T.-Y., Natarajan S., Chu X.-J., Bräse S., Rübsam F. Chem. Eur. J. 5:1999;2584-2601 (e) Nicolaou K.C., Boddy C.N.C., Li H., Koumbis A.E., Hughes R., Natarajan S., Jain N.F., Ramanjulu J.M., Bräse S., Solomon M.E. Chem. Eur. J. 5:1999;2602-2621 (f) Nicolaou K.C., Koumbis A.E., Takayanagi M., Natarajan S., Jain N.F., Bando T., Li H., Hughes R. Chem. Eur. J. 5:1999;2622-2647 (g) Nicolaou K.C., Mitchell H.J., Jain N.F., Bando T., Hughes R., Winssinger N., Natarajan S., Koumbis A.E. Chem. Eur. J. 5:1999;2648-2667 (h) Evans D.A., Wood M.R., Trotter B.W., Richardson T.I., Barrow J.C., Katz J.L. Angew. Chem., Int. Ed. 37:1998;2700-2704.
5. For a review, see: (a) Nicolaou K.C., Boddy C.N.C., Bräse S., Winssinger N. Angew. Chem., Int. Ed. 38:1999;2096-2152 (b) Boger D.L., Miyazaki S., Kim S.H., Wu J.H., Castle S.L., Loiseleur O., Jin Q. J. Am. Chem. Soc. 121:1999;10004-10011 (c) Boger D.L., Kim S.H., Mori Y., Weng J.-H., Rogel O., Castle S.L., McAtee J.J. J. Am. Chem. Soc. 123:2001;1862-1871 (d) Nicolaou K.C., Li H., Boddy C.N.C., Ramanjulu J.M., Yue T.-Y., Natarajan S., Chu X.-J., Bräse S., Rübsam F. Chem. Eur. J. 5:1999;2584-2601 (e) Nicolaou K.C., Boddy C.N.C., Li H., Koumbis A.E., Hughes R., Natarajan S., Jain N.F., Ramanjulu J.M., Bräse S., Solomon M.E. Chem. Eur. J. 5:1999;2602-2621 (f) Nicolaou K.C., Koumbis A.E., Takayanagi M., Natarajan S., Jain N.F., Bando T., Li H., Hughes R. Chem. Eur. J. 5:1999;2622-2647 (g) Nicolaou K.C., Mitchell H.J., Jain N.F., Bando T., Hughes R., Winssinger N., Natarajan S., Koumbis A.E. Chem. Eur. J. 5:1999;2648-2667 (h) Evans D.A., Wood M.R., Trotter B.W., Richardson T.I., Barrow J.C., Katz J.L. Angew. Chem., Int. Ed. 37:1998;2700-2704.
6. For a review, see: (a) Nicolaou K.C., Boddy C.N.C., Bräse S., Winssinger N. Angew. Chem., Int. Ed. 38:1999;2096-2152 (b) Boger D.L., Miyazaki S., Kim S.H., Wu J.H., Castle S.L., Loiseleur O., Jin Q. J. Am. Chem. Soc. 121:1999;10004-10011 (c) Boger D.L., Kim S.H., Mori Y., Weng J.-H., Rogel O., Castle S.L., McAtee J.J. J. Am. Chem. Soc. 123:2001;1862-1871 (d) Nicolaou K.C., Li H., Boddy C.N.C., Ramanjulu J.M., Yue T.-Y., Natarajan S., Chu X.-J., Bräse S., Rübsam F. Chem. Eur. J. 5:1999;2584-2601 (e) Nicolaou K.C., Boddy C.N.C., Li H., Koumbis A.E., Hughes R., Natarajan S., Jain N.F., Ramanjulu J.M., Bräse S., Solomon M.E. Chem. Eur. J. 5:1999;2602-2621 (f) Nicolaou K.C., Koumbis A.E., Takayanagi M., Natarajan S., Jain N.F., Bando T., Li H., Hughes R. Chem. Eur. J. 5:1999;2622-2647 (g) Nicolaou K.C., Mitchell H.J., Jain N.F., Bando T., Hughes R., Winssinger N., Natarajan S., Koumbis A.E. Chem. Eur. J. 5:1999;2648-2667 (h) Evans D.A., Wood M.R., Trotter B.W., Richardson T.I., Barrow J.C., Katz J.L. Angew. Chem., Int. Ed. 37:1998;2700-2704.
7. For a review, see: (a) Nicolaou K.C., Boddy C.N.C., Bräse S., Winssinger N. Angew. Chem., Int. Ed. 38:1999;2096-2152 (b) Boger D.L., Miyazaki S., Kim S.H., Wu J.H., Castle S.L., Loiseleur O., Jin Q. J. Am. Chem. Soc. 121:1999;10004-10011 (c) Boger D.L., Kim S.H., Mori Y., Weng J.-H., Rogel O., Castle S.L., McAtee J.J. J. Am. Chem. Soc. 123:2001;1862-1871 (d) Nicolaou K.C., Li H., Boddy C.N.C., Ramanjulu J.M., Yue T.-Y., Natarajan S., Chu X.-J., Bräse S., Rübsam F. Chem. Eur. J. 5:1999;2584-2601 (e) Nicolaou K.C., Boddy C.N.C., Li H., Koumbis A.E., Hughes R., Natarajan S., Jain N.F., Ramanjulu J.M., Bräse S., Solomon M.E. Chem. Eur. J. 5:1999;2602-2621 (f) Nicolaou K.C., Koumbis A.E., Takayanagi M., Natarajan S., Jain N.F., Bando T., Li H., Hughes R. Chem. Eur. J. 5:1999;2622-2647 (g) Nicolaou K.C., Mitchell H.J., Jain N.F., Bando T., Hughes R., Winssinger N., Natarajan S., Koumbis A.E. Chem. Eur. J. 5:1999;2648-2667 (h) Evans D.A., Wood M.R., Trotter B.W., Richardson T.I., Barrow J.C., Katz J.L. Angew. Chem., Int. Ed. 37:1998;2700-2704.
8. For a review, see: (a) Nicolaou K.C., Boddy C.N.C., Bräse S., Winssinger N. Angew. Chem., Int. Ed. 38:1999;2096-2152 (b) Boger D.L., Miyazaki S., Kim S.H., Wu J.H., Castle S.L., Loiseleur O., Jin Q. J. Am. Chem. Soc. 121:1999;10004-10011 (c) Boger D.L., Kim S.H., Mori Y., Weng J.-H., Rogel O., Castle S.L., McAtee J.J. J. Am. Chem. Soc. 123:2001;1862-1871 (d) Nicolaou K.C., Li H., Boddy C.N.C., Ramanjulu J.M., Yue T.-Y., Natarajan S., Chu X.-J., Bräse S., Rübsam F. Chem. Eur. J. 5:1999;2584-2601 (e) Nicolaou K.C., Boddy C.N.C., Li H., Koumbis A.E., Hughes R., Natarajan S., Jain N.F., Ramanjulu J.M., Bräse S., Solomon M.E. Chem. Eur. J. 5:1999;2602-2621 (f) Nicolaou K.C., Koumbis A.E., Takayanagi M., Natarajan S., Jain N.F., Bando T., Li H., Hughes R. Chem. Eur. J. 5:1999;2622-2647 (g) Nicolaou K.C., Mitchell H.J., Jain N.F., Bando T., Hughes R., Winssinger N., Natarajan S., Koumbis A.E. Chem. Eur. J. 5:1999;2648-2667 (h) Evans D.A., Wood M.R., Trotter B.W., Richardson T.I., Barrow J.C., Katz J.L. Angew. Chem., Int. Ed. 37:1998;2700-2704.
9. For a stereoselective total systhesis of (+)-lactacystin, see: Nagamitsu T., Sunazuka T., Tanaka H., Ōmura S., Sprengeler P.A., Smith A.B. III. J. Am. Chem. Soc. 118:1996;3584-3590.
10. For a recent example of a diastereoselective synthesis of γ-hydroxy-β-amino alcohols from a serine derivative, see: Laïb T., Chastanet J., Zhu J. J. Org. Chem. 63:1998;1709-1713.
11. For pioneer works, see: (a) Mattingly P.G., Kerwin J.F. Jr., Miller M.J. J. Am. Chem. Soc. 101:1979;3983-3985 (b) Floyd D.M., Fritz A.W., Pluscec J., Weaver E.R., Cimarusti C.M. J. Org. Chem. 47:1982;5160-5167 (c) Teng M., Miller M.J. J. Am. Chem. Soc. 115:1993;548-554 (d). For a recent example, see: Jackson B.G., Pedersen S.W., Fisher J.W., Misner J.W., Gardner J.P., Staszak M.A., Doecke C., Rizzo J., Aikins J., Farkas E., Trinkle K.L., Vicenzi J., Reinhard M., Kroeff E.P., Higginbotham C.A., Gazak R.J., Zhang T.Y. Tetrahedron. 56:2000;5667-5677.
12. For pioneer works, see: (a) Mattingly P.G., Kerwin J.F. Jr., Miller M.J. J. Am. Chem. Soc. 101:1979;3983-3985 (b) Floyd D.M., Fritz A.W., Pluscec J., Weaver E.R., Cimarusti C.M. J. Org. Chem. 47:1982;5160-5167 (c) Teng M., Miller M.J. J. Am. Chem. Soc. 115:1993;548-554 (d). For a recent example, see: Jackson B.G., Pedersen S.W., Fisher J.W., Misner J.W., Gardner J.P., Staszak M.A., Doecke C., Rizzo J., Aikins J., Farkas E., Trinkle K.L., Vicenzi J., Reinhard M., Kroeff E.P., Higginbotham C.A., Gazak R.J., Zhang T.Y. Tetrahedron. 56:2000;5667-5677.
13. For pioneer works, see: (a) Mattingly P.G., Kerwin J.F. Jr., Miller M.J. J. Am. Chem. Soc. 101:1979;3983-3985 (b) Floyd D.M., Fritz A.W., Pluscec J., Weaver E.R., Cimarusti C.M. J. Org. Chem. 47:1982;5160-5167 (c) Teng M., Miller M.J. J. Am. Chem. Soc. 115:1993;548-554 (d). For a recent example, see: Jackson B.G., Pedersen S.W., Fisher J.W., Misner J.W., Gardner J.P., Staszak M.A., Doecke C., Rizzo J., Aikins J., Farkas E., Trinkle K.L., Vicenzi J., Reinhard M., Kroeff E.P., Higginbotham C.A., Gazak R.J., Zhang T.Y. Tetrahedron. 56:2000;5667-5677.
14. For pioneer works, see: (a) Mattingly P.G., Kerwin J.F. Jr., Miller M.J. J. Am. Chem. Soc. 101:1979;3983-3985 (b) Floyd D.M., Fritz A.W., Pluscec J., Weaver E.R., Cimarusti C.M. J. Org. Chem. 47:1982;5160-5167 (c) Teng M., Miller M.J. J. Am. Chem. Soc. 115:1993;548-554 (d). For a recent example, see: Jackson B.G., Pedersen S.W., Fisher J.W., Misner J.W., Gardner J.P., Staszak M.A., Doecke C., Rizzo J., Aikins J., Farkas E., Trinkle K.L., Vicenzi J., Reinhard M., Kroeff E.P., Higginbotham C.A., Gazak R.J., Zhang T.Y. Tetrahedron. 56:2000;5667-5677.
15. Buono G., Siv C., Peiffer G., Triantaphylides C., Denis P., Mortreux A., Petit F. J. Org. Chem. 50:1985;1781-1782.
16. Righi G., Rumboldt G., Bonini C. Tetrahedron. 51:1995;13401-13408. See also Ref. 2.
17. Tao B., Schlingloff G., Sharpless K.B. Tetrahedron Lett. 39:1998;2507-2510
18. (b) Park H., Cao B., Joullié M.M. J. Org. Chem. 66:2001;7223-7226. See also Ref. 1e.
19. Kim B.M., Sharpless K.B. Tetrahedron Lett. 31:1990;4317-4320.
20. (b) Shao H., Goodman M. J. Org. Chem. 61:1996;2582-2583. See also Ref. 1e.
21. Blaskovich M.A., Evindar G., Rose N.G.W., Wilkinson S., Luo Y., Lajoie G.A. J. Org. Chem. 63:1998;3631-3646
22. (b) Avenoza A., Cativiela C., Corzana F., Peregrina J.M., Zurbano M.M. Tetrahedron: Asymmetry. 11:2000;2195-2204.
23. (c) Williams L., Zhang Z., Shao F., Carroll P.J., Joullié M.M. Tetrahedron. 52:1996;11673-11694.
24. Kuwano R., Okuda S., Ito Y. J. Org. Chem. 63:1998;3499-3503.
25. Noyori R., Ikeda T., Ohkuma T., Widhalm M., Kitamura M., Takaya H., Akutagawa S., Sayo N., Saito T., Taketomi T., Kumobayashi H. J. Am. Chem. Soc. 111:1989;9134-9135.
26. Merino P., Franco S., Merchan F.L., Tejero T. Tetrahedron: Asymmetry. 8:1997;3489-3496.
27. Davis F.A., Srirajan V., Fanelli D.L., Portonovo P. J. Org. Chem. 65:2000;7663-7666.
28. Ruble J.C., Fu G.C. J. Am. Chem. Soc. 120:1998;11532-11533.
29. Belokon Y.N., Kochetkov K.A., Ikonnikov N.S., Strelkova T.V., Harutyunyan S.R., Saghiyan A.S. Tetrahedron: Asymmetry. 12:2001;481-485.
30. (b) Caddick S., Parr N.J., Pritchard M.C. Tetrahedron Lett. 41:2000;5963-5966.
31. (c) Felice P.D., Porzi G., Sandri S. Tetrahedron: Asymmetry. 10:1999;2191-2201.
32. (d) Alker D., Hamblett G., Harwood L.M., Robertson S.M., Watkin D.J., Williams C.E. Tetrahedron. 54:1998;6089-6098.
33. (e) Iwanowicz E.J., Blomgren P., Cheng P.T.W., Smith K., Lau W.F., Pan Y.Y., Gu H.H., Malley M.F., Gougoutas J.Z. Synlett. 1998;664-666.
34. (f) Kanemasa S., Mori T., Wada E., Tatsukawa A. Tetrahedron Lett. 34:1993;677-680.
35. (g) Corey E.J., Lee D.-H., Choi S. Tetrahedron Lett. 33:1992;6735-6738.
36. (h) Gasparski C.M., Miller M.J. Tetrahedron. 47:1991;5367-5378.
37. (i) Bold G., Duthaler R.O., Riediker M. Angew. Chem., Int. Ed. Engl. 28:1989;497-498.
38. (j) Evans D.A., Sjogren E.B., Weber A.E., Conn R.E. Tetrahedron Lett. 28:1987;39-42.
39. (k) Evans D.A., Weber A.E. J. Am. Chem. Soc. 108:1986;6757-6761.
40. (l) Belokon Y.N., Bulychev A.G., Vitt S.V., Struchkov Y.T., Batsanov A.S., Timofeeva T.V., Tsyryapkin V.A., Ryzhov M.G., Lysova L.A., Bakhmutov V.I., Belikov V.M. J. Am. Chem. Soc. 107:1985;4252-4259.
41. (m) Schöllkopf U. Tetrahedron. 39:1983;2085-2091.
42. (n) Nakatsuka T., Miwa T., Mukaiyama T. Chem. Lett. 1981;279-282. See also Ref. 16-19.
43. (a) Sawamura M., Nakayama Y., Kato T., Ito Y. J. Org. Chem. 60:1995;1727-1732.
44. (b) Ito Y., Sawamura M., Shirakawa E., Hayashizaki K., Hayashi T. Tetrahedron. 44:1988;5253-5262.
45. (c) Ito Y., Sawamura M., Shirakawa E., Hayashizaki K., Hayashi T. Tetrahedron Lett. 29:1988;235-238.
46. (d) Ito Y., Sawamura M., Hayashi T. J. Am. Chem. Soc. 108:1986;6405-6406.
47. Horikawa M., Busch-Petersen J., Corey E.J. Tetrahedron Lett. 40:1999;3843-3846.
48. Suga H., Ikai K., Ibata T. Tetrahedron Lett. 39:1998;869-879.
49. (b) Evans D.A., Janey J.M., Magomedov N., Tedrow J.S. Angew. Chem., Int. Ed. 40:2001;1884-1888.
50. Kimura T., Vassilev V.P., Shen G.-J., Wong C.-H. J. Am. Chem. Soc. 119:1997;11734-11742.
51. Yoshikawa N., Suzuki T., Shibasaki M. J. Org. Chem. 67:2002;2556-2565.
52. (b) Yoshikawa N., Kumagai N., Matsunaga S., Moll G., Ohshima T., Suzuki T., Shibasaki M. J. Am. Chem. Soc. 123:2001;2466-2467.
53. (c) Yoshikawa N., Shibasaki M. Tetrahedron. 57:2001;2569-2579.
54. (d) Yoshikawa N., Yamada Y.M.A., Das J., Sasai H., Shibasaki M. J. Am. Chem. Soc. 121:1999;4168-4178.
55. (e) Yamada Y.M.A., Yoshikawa N., Sasai H., Shibasaki M. Angew. Chem., Int. Ed. Engl. 36:1997;1871-1873.
56. For a review of catalytic asymmetric direct aldol reactions, see: Alcaide B., Almendros P. Eur. J. Org. Chem. 2002;1595-1601.
57. For reviews of enantioselective transformations catalyzed by heterobimetallic complexes, see: (a) Shibasaki M., Yoshikawa N. Chem. Rev. 102:2002;2187-2209 (b) Shibasaki M., Yamada K.-, Yoshikawa N. Yamamoto H., Lewis Acids in Organic Synthesis. Vol. 2:2000;Wiley-VCH, Weinheim. Chapter 20 (c) Shibasaki M. Enantiomer. 4:1999;513-527 (d) Shibasaki M. Chemtracts-Org. Chem. 12:1999;979-998 (e) Shibasaki M., Iida T., Yamada Y.M.A. J. Synth. Org. Chem. Jpn. 56:1998;344-356 (f) Shibasaki M., Sasai H., Arai T., Iida T. Pure Appl. Chem. 70:1998;1027-1034 (g) Shibasaki M., Sasai H., Arai T. Angew. Chem., Int. Ed. Engl. 36:1997;1236-1256.
58. For reviews of enantioselective transformations catalyzed by heterobimetallic complexes, see: (a) Shibasaki M., Yoshikawa N. Chem. Rev. 102:2002;2187-2209 (b) Shibasaki M., Yamada K.-, Yoshikawa N. Yamamoto H., Lewis Acids in Organic Synthesis. Vol. 2:2000;Wiley-VCH, Weinheim. Chapter 20 (c) Shibasaki M. Enantiomer. 4:1999;513-527 (d) Shibasaki M. Chemtracts-Org. Chem. 12:1999;979-998 (e) Shibasaki M., Iida T., Yamada Y.M.A. J. Synth. Org. Chem. Jpn. 56:1998;344-356 (f) Shibasaki M., Sasai H., Arai T., Iida T. Pure Appl. Chem. 70:1998;1027-1034 (g) Shibasaki M., Sasai H., Arai T. Angew. Chem., Int. Ed. Engl. 36:1997;1236-1256.
59. For reviews of enantioselective transformations catalyzed by heterobimetallic complexes, see: (a) Shibasaki M., Yoshikawa N. Chem. Rev. 102:2002;2187-2209 (b) Shibasaki M., Yamada K.-, Yoshikawa N. Yamamoto H., Lewis Acids in Organic Synthesis. Vol. 2:2000;Wiley-VCH, Weinheim. Chapter 20 (c) Shibasaki M. Enantiomer. 4:1999;513-527 (d) Shibasaki M. Chemtracts-Org. Chem. 12:1999;979-998 (e) Shibasaki M., Iida T., Yamada Y.M.A. J. Synth. Org. Chem. Jpn. 56:1998;344-356 (f) Shibasaki M., Sasai H., Arai T., Iida T. Pure Appl. Chem. 70:1998;1027-1034 (g) Shibasaki M., Sasai H., Arai T. Angew. Chem., Int. Ed. Engl. 36:1997;1236-1256.
60. For reviews of enantioselective transformations catalyzed by heterobimetallic complexes, see: (a) Shibasaki M., Yoshikawa N. Chem. Rev. 102:2002;2187-2209 (b) Shibasaki M., Yamada K.-, Yoshikawa N. Yamamoto H., Lewis Acids in Organic Synthesis. Vol. 2:2000;Wiley-VCH, Weinheim. Chapter 20 (c) Shibasaki M. Enantiomer. 4:1999;513-527 (d) Shibasaki M. Chemtracts-Org. Chem. 12:1999;979-998 (e) Shibasaki M., Iida T., Yamada Y.M.A. J. Synth. Org. Chem. Jpn. 56:1998;344-356 (f) Shibasaki M., Sasai H., Arai T., Iida T. Pure Appl. Chem. 70:1998;1027-1034 (g) Shibasaki M., Sasai H., Arai T. Angew. Chem., Int. Ed. Engl. 36:1997;1236-1256.
61. For reviews of enantioselective transformations catalyzed by heterobimetallic complexes, see: (a) Shibasaki M., Yoshikawa N. Chem. Rev. 102:2002;2187-2209 (b) Shibasaki M., Yamada K.-, Yoshikawa N. Yamamoto H., Lewis Acids in Organic Synthesis. Vol. 2:2000;Wiley-VCH, Weinheim. Chapter 20 (c) Shibasaki M. Enantiomer. 4:1999;513-527 (d) Shibasaki M. Chemtracts-Org. Chem. 12:1999;979-998 (e) Shibasaki M., Iida T., Yamada Y.M.A. J. Synth. Org. Chem. Jpn. 56:1998;344-356 (f) Shibasaki M., Sasai H., Arai T., Iida T. Pure Appl. Chem. 70:1998;1027-1034 (g) Shibasaki M., Sasai H., Arai T. Angew. Chem., Int. Ed. Engl. 36:1997;1236-1256.
62. For reviews of enantioselective transformations catalyzed by heterobimetallic complexes, see: (a) Shibasaki M., Yoshikawa N. Chem. Rev. 102:2002;2187-2209 (b) Shibasaki M., Yamada K.-, Yoshikawa N. Yamamoto H., Lewis Acids in Organic Synthesis. Vol. 2:2000;Wiley-VCH, Weinheim. Chapter 20 (c) Shibasaki M. Enantiomer. 4:1999;513-527 (d) Shibasaki M. Chemtracts-Org. Chem. 12:1999;979-998 (e) Shibasaki M., Iida T., Yamada Y.M.A. J. Synth. Org. Chem. Jpn. 56:1998;344-356 (f) Shibasaki M., Sasai H., Arai T., Iida T. Pure Appl. Chem. 70:1998;1027-1034 (g) Shibasaki M., Sasai H., Arai T. Angew. Chem., Int. Ed. Engl. 36:1997;1236-1256.
63. For reviews of enantioselective transformations catalyzed by heterobimetallic complexes, see: (a) Shibasaki M., Yoshikawa N. Chem. Rev. 102:2002;2187-2209 (b) Shibasaki M., Yamada K.-, Yoshikawa N. Yamamoto H., Lewis Acids in Organic Synthesis. Vol. 2:2000;Wiley-VCH, Weinheim. Chapter 20 (c) Shibasaki M. Enantiomer. 4:1999;513-527 (d) Shibasaki M. Chemtracts-Org. Chem. 12:1999;979-998 (e) Shibasaki M., Iida T., Yamada Y.M.A. J. Synth. Org. Chem. Jpn. 56:1998;344-356 (f) Shibasaki M., Sasai H., Arai T., Iida T. Pure Appl. Chem. 70:1998;1027-1034 (g) Shibasaki M., Sasai H., Arai T. Angew. Chem., Int. Ed. Engl. 36:1997;1236-1256.
64. For recent reviews of aldol reactions of modified carbonyl compounds (Mukaiyama aldol reaction), see: (a) Carreira E.M. Ojima I., Catalytic Asymmetric Synthesis. 2nd ed. 2000;Wiley, New York. Chapter 8B2 (b) Sawamura M., Ito Y. Ojima I., Catalytic Asymmetric Synthesis. 2nd ed. 2000;Wiley, New York. Chapter 8B1 (c) Machajewski T.D., Wong C.-H. Angew. Chem., Int. Ed. 39:2000;1352-1374 (d) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357-389 (e) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137-1141.
65. For recent reviews of aldol reactions of modified carbonyl compounds (Mukaiyama aldol reaction), see: (a) Carreira E.M. Ojima I., Catalytic Asymmetric Synthesis. 2nd ed. 2000;Wiley, New York. Chapter 8B2 (b) Sawamura M., Ito Y. Ojima I., Catalytic Asymmetric Synthesis. 2nd ed. 2000;Wiley, New York. Chapter 8B1 (c) Machajewski T.D., Wong C.-H. Angew. Chem., Int. Ed. 39:2000;1352-1374 (d) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357-389 (e) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137-1141.
66. For recent reviews of aldol reactions of modified carbonyl compounds (Mukaiyama aldol reaction), see: (a) Carreira E.M. Ojima I., Catalytic Asymmetric Synthesis. 2nd ed. 2000;Wiley, New York. Chapter 8B2 (b) Sawamura M., Ito Y. Ojima I., Catalytic Asymmetric Synthesis. 2nd ed. 2000;Wiley, New York. Chapter 8B1 (c) Machajewski T.D., Wong C.-H. Angew. Chem., Int. Ed. 39:2000;1352-1374 (d) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357-389 (e) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137-1141.
67. For recent reviews of aldol reactions of modified carbonyl compounds (Mukaiyama aldol reaction), see: (a) Carreira E.M. Ojima I., Catalytic Asymmetric Synthesis. 2nd ed. 2000;Wiley, New York. Chapter 8B2 (b) Sawamura M., Ito Y. Ojima I., Catalytic Asymmetric Synthesis. 2nd ed. 2000;Wiley, New York. Chapter 8B1 (c) Machajewski T.D., Wong C.-H. Angew. Chem., Int. Ed. 39:2000;1352-1374 (d) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357-389 (e) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137-1141.
68. For recent reviews of aldol reactions of modified carbonyl compounds (Mukaiyama aldol reaction), see: (a) Carreira E.M. Ojima I., Catalytic Asymmetric Synthesis. 2nd ed. 2000;Wiley, New York. Chapter 8B2 (b) Sawamura M., Ito Y. Ojima I., Catalytic Asymmetric Synthesis. 2nd ed. 2000;Wiley, New York. Chapter 8B1 (c) Machajewski T.D., Wong C.-H. Angew. Chem., Int. Ed. 39:2000;1352-1374 (d) Nelson S.G. Tetrahedron: Asymmetry. 9:1998;357-389 (e) Gröger H., Vogl E.M., Shibasaki M. Chem. Eur. J. 4:1998;1137-1141.
69. For catalytic asymmetric alkylations of glycinate Schiff bases, see: (a) O'Donnell M.J., Wu S., Huffman J.C. Tetrahedron. 50:1994;4507-4518 (b) Ooi T., Takeuchi M., Kameda M., Maruoka K. J. Am. Chem. Soc. 122:2000;5228-5229. and references cited therein.
70. For catalytic asymmetric alkylations of glycinate Schiff bases, see: (a) O'Donnell M.J., Wu S., Huffman J.C. Tetrahedron. 50:1994;4507-4518 (b) Ooi T., Takeuchi M., Kameda M., Maruoka K. J. Am. Chem. Soc. 122:2000;5228-5229. and references cited therein.
71. Arai T., Yamada Y.M.A., Yamamoto N., Sasai H., Shibasaki M. Chem. Eur. J. 2:1996;1368-1372. See also Refs. 20a,b,d and 22.
72. The use of heterobimetallic complexes containing other lanthanide (Pr, Sm, Gd, Dy, or Yb) gave similar results, in contrast to the previous report: Sasai H., Suzuki T., Itoh N., Arai S., Shibasaki M. Tetrahedron Lett. 34:1993;2657-2660.
73. The enantiomeric excess of the oxazolidines was comparable to that of syn-3. Corey et al. also reported the formation of oxazolidines in aldol reactions. See Ref. 17.
74. Miller et al. have obtained 12% ee. See Ref. 15h.
75. (a) O'Donnell M.J., Polt R.L. J. Org. Chem. 47:1982;2663-2666
76. (b) Pickard P.L., Tolbert T.L. Organic Syntheses. Collect. Vol. V:1973;Wiley, New York. pp 520-522.