Direct catalytic asymmetric aldol reactions promoted by a novel barium complex

Tetrahedron Letters

Volumn 39, Issue 31, 1998, Pages 5561-5564

  Yamada, Yoichi M A ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Aldol reactions; Asymmetric catalysis; Barium and compounds; Unmodified ketones

Indexed keywords

ALDEHYDE; BARIUM DERIVATIVE; KETONE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; MASS SPECTROMETRY; REACTION ANALYSIS;

EID: 0032581554     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01120-4     Document Type: Article

References (23)

1. [1] For reviews, see a) Nelson SG, Tetrahedron: Asymmetry 1998;9:357-389;
2. b) Gröger H, Vogl EM, Shibasaki M, Chem. Eur. J. 1998;4:1135-1139.
3. [2] Yamada YMA, Yoshikawa N, Sasai H, Shibasaki M, Angew. Chem. Int. Ed. Engl. 1997;36:1871-1873.
4. [3] For reviews on heterobimetallic catalysts, see a) Shibasaki M, Sasai H, Arai T, Angew. Chem. Int. Ed. Engl. 1997;36:1236-1256;
5. b) Steinhagen H, Helmchen G, Angew. Chem. Int. Ed. Engl. 1996;35:2339-2342;
6. c) Shibasaki M, Iida T, Yamada YMA, J. Synth. Org. Chem. Jpn. 1998;56:344-356.
7. 2 catalyzed reactions, see a) Parshall GW, Ittel SD, Homogeneous Catalysis, 2nd Ed., Wiley, New York, 1992;
8. b) Ai M, Bull. Chem. Soc. Jpn. 1991;64:1342-1345:
9. c) Zhang G, Hattori H, Tanabe K, Appl. Catal. 1988;36:189-197;
10. d) Gercia-Raso A, Sinisterra JV, Marinas J, Pol. J. Chem. 1982;56:1435-1445;
11. e) Gong Y-D, Kurth MJ, Tetrahedron Lett. 1998;39:3379-3382.
12. [5] Yamamoto et al. suggested a coordination of an aldehyde to an allylic barium reagent; see a) Yanagisawa A, Yamada Y, Yamamoto H, Synlett 1997;1090-1092;
13. b) Yanagisawa A, Habaue S, Yasue K, Yamamoto H, J. Am. Chem. Soc. 1994;116:6130-6141, and references cited therein.
14. [6] Caulton KG, Chisholm MH, Drake SR, Folting K, Huffman JC, Streib WE, Inorg. Chem. 1993;32:1970-1976, and references cited therein.
15. [7] Huang L, Turnipseed SB, Haltiwanger RC, Barkley RM, Sievers RE, Inorg. Chem. 1994: 33:798-803, and references cited therein.
16. [8] For other applications of BINOL-Me, see a) Ishihara K, Nakamura S, Kaneeda M, Yamamoto H, J. Am. Chem. Soc. 1996;118:12854-12855;
17. b) Taniguchi T, Ogasawara K, Tetrahedron Lett. 1997;38:6429-6432, and references cited therein.
18. [9] Blanchette MA, Malamas MS, Nantz MH, Roberts JC, Somfai P, Whritenour DC, Masamune S, J. Org. Chem. 1989;54:2817-2825, and references cited therein.
19. [10] The absolute configurations of 3e and 3f were determined by Mosher's method to be (S)-form; see Dale JA. Mosher HS, J. Am. Chem. Soc. 1973;95:512-519; The enantiomeric excess of 3e and 3f was determined by HPLC analysis using DAICEL CHIRALPAK AS. For other adducts, see ref [2].
20. [11] a) Sasai H, Suzuki T, Itoh N, Tanaka K, Date T, Okamura K, Shibasaki M, J. Am. Chem. Soc. 1993;115:10372-10373;
21. b) Gröger H, Saida Y, Sasai H, Yamaguchi K, Martens J, Shibasaki M, J. Am. Chem. Soc. 1998;120:3089-3103.
22. [12] Arai T, Yamada YMA, Yamamoto N, Sasai H, Shibasaki M, Chem. Eur. J. 1996;2:1368-1372.
23. [13] For review, see Avalos M, Babiano R, Cintas P, Jiménez JL, Palacios JC, Tetrahedron: Asymmetry 1997;8:2997-3017.