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Volumn 121, Issue 21, 1999, Pages 4982-4991

Chiral phosphoramide-catalyzed aldol additions of ketone enolates. Preparative aspects

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; PHOSPHORAMIDIC ACID; SILANE DERIVATIVE;

EID: 0033516307     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984123j     Document Type: Article
Times cited : (117)

References (97)
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    • (c) In situ generated dimethyl(triflato)silyl enolates are claimed to engage in uncatalyzed aldol reactions, see: Kobayashi, S.; Nishio, K. J. Org. Chem. 1993, 58, 2647.
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    • note
    • The presence of 4 A molecular sieves in the reaction mixture has no apparent effect on the selectivity of the process, although they may prevent elimination of the trichlorosilyl aldolate.
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    • All X-ray crystal structure data has been deposited in the Cambridge Crystallographic Data Center as supplementary publication Nos. CCDC-111716 ((+)-anti-10), CCDC-111826 ((+)-syn-19), CCDC-111715 ((+)-syn-4b). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk)
    • All X-ray crystal structure data has been deposited in the Cambridge Crystallographic Data Center as supplementary publication Nos. CCDC-111716 ((+)-anti-10), CCDC-111826 ((+)-syn-19)), CCDC-111715 ((+)-syn-4b)). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
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    • For reactions of alkylsilyl enol ethers under mild conditions, see: (a) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741. (b) RajanBabu, T. V. J. Org. Chem. 1984, 49, 2083.
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    • For reactions of alkylsilyl enol ethers under mild conditions, see: (a) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741. (b) RajanBabu, T. V. J. Org. Chem. 1984, 49, 2083.
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    • unpublished results from these laboratories
    • Winter, S. D. W.; Stavenger, R. A., unpublished results from these laboratories.
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    • note
    • This notation is used to describe the faces of the enol double bond relative to the C(1) (oxygen-bearing) position, rather than the more typical C(2) position which is actually transformed into the resultant tetrahedral center.


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