The formyl C-H--O hydrogen bond as a critical factor in enantioselective reactions of aldehydes, Part 4, aldol, ethylation, hydrocyanation and Diels-Alder reactions catalyzed by chiral Bb, Ti and a1 Lewis acids

Tetrahedron Letters

Volumn 38, Issue 25, 1997, Pages 4351-4354

  Corey, E J ^a   Barnes Seeman, David ^a   Lee, Thomas W ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; HYDROGEN BOND;

BETULACEAE;

EID: 0030913422     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00932-5     Document Type: Article

References (21)

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2. Corey, E. J.; Rohde, J. J. Tetrahedron Letters 1997, 38, 37.
3. Corey, E. J.; Barnes-Seeman, D.; Lee, T. W. Tetrahedron Letters 1997, 38, 1699.
4. (a) Kiyooka, S.-i.; Kaneko, Y.; Kume, K.-i. Tetrahedron Letters 1992, 34, 4927.
5. (b) Kiyooka, S.-i.; Hena, M. A. Tetrahedron: Asymmetry 1996, 7, 2181.
6. (c) Kiyooka, S.-i.; Kaneko, Y.; Komura, M.; Matsuo, H.; Nakano, M. J. Org. Chem. 1991, 56, 2276.
7. Stereopair diagrams 1-6 were generated with CSC Chem3D Plus™ (standard bond distances and angles).
8. An analysis similar to that summarized in Figure 1 can be used to explain the results of Masamune et al. for enantioselective aldol reactions of related oxazaborolidine catalysts. See (a) Parmee, E. R.; Tempkin, O.; Masamune, S.; Abiko, A. J. Am. Chem. Soc. 1991, 113, 9365.
9. (b) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Letters 1992, 33, 1729.
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11. Minamikawa, H.; Hayakawa, S.; Yamada, T.; Iwasawa, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1988, 61, 4379.
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14. (b) Hayashi, M.; Kaneda, H.; Oguni, N. Tetrahedron: Asymmetry 1995, 6, 2511.
15. (c) Hayashi, M.; Inoue, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1994, 341.
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21. This research was supported by grants from the National Science Foundation and the National Institutes of Health. D.B.-S. and T.W.L. are Graduate Fellows of the National Science Foundation.