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Volumn 9, Issue 3, 1998, Pages 357-389

Catalyzed enantioselective aldol additions of latent enolate equivalents

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CATALYSIS; CHIRALITY; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; COVALENT BOND; CRYSTAL STRUCTURE; ENANTIOMER; LIGAND BINDING; PRIORITY JOURNAL; PROTEIN ANALYSIS; REACTION ANALYSIS;

EID: 0032512595     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00634-4     Document Type: Article
Times cited : (439)

References (95)
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    • 9. For a recent application of related chiral Sn(II)-diamine promoters to aldol additions employing β-alkoxy silyl ketene acetals, see: Kobayashi, S.; Horibe, M. J. Am. Chem. Soc. 1994, 116, 9805-9806.
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    • 17. The term 'CAB' is used in Ref. 16a as an acronym for 'chiral (acyloxy)borane' and is used herein for the purposes of convenience.
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    • 39. Non-chelated Lewis acid-glyoxylate complexes have been envoked to rationalize the syn diastereoselection derived from related Lewis acid promoted ene reactions, see: Mikami, K.; Loh, T.-P.; Nakai, T. Tetrahedron Lett. 1988, 29, 6305-6308.
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    • 40. While the addition of enol silane 59 via an open transition state seemingly does not accomodate the formal ene-type products that emerge from these reactions, this fact does not necessarily preclude the intervention of the non-concerted reaction pathway represented by an open transition state structure.
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    • 54. Lewis acid promoted additions of enol silanes to chiral β-alkoxy aldehydes, transformations analogous to the reaction depicted in Eq. 23, afford the 1,3-anti aldol diastereomer selectively. See: Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G. J. Am. Chem. Soc. 1996, 118, 4322-4343.
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    • note
    • 61. Despite the organizational scheme of this review, these Sn(II) catalysts are discussed here to allow a more effective comparison to the structurally related Cu(II)-bisoxazoline catalyst complexes discussed in the preceeding section.
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    • 65. For a detailed investigation of Rh(I)-catalyzed addition reactions of silyl enol ethers that involve nucleophile rather than electrophile activation, see: Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938-949.
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    • 66. Lewis base accelerated aldehyde additions of allylic trichlorosilanes have been reported, see: (a) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163.
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    • note
    • 70. The author wishes to thank a referee for suggesting the relevance of this process to catalyzed additions of latent enolates.


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