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Volumn 39, Issue 15, 2000, Pages 2736-2737

Enantioselective generation of benzylic stereocenters mediated by a remote sulfoxide

Author keywords

Carbanions; Lithium; Sulfoxides; Sulfur

Indexed keywords

BENZILIC ACID; SULFOXIDE;

EID: 0034604563     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000804)39:15<2736::AID-ANIE2736>3.0.CO;2-M     Document Type: Article
Times cited : (59)

References (26)
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    • note
    • Characterization of 5a was carried out immediately after crystallization since it readily epimerizes at C-2.
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    • note
    • The structures of 8a and 10a were established by X-ray diffraction. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications nos. CCDC-139404 and -139405. 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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    • note
    • 1 is consistent with the result observed when reaction of 3 with acetone (entry 3) was conducted in the presence of hexamethylphosphoric triamide (6 equiv). Under these conditions, an 87;13 mixture of 7a and its epimer at the benzylic carbon atom was isolated.


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