Journal article

Oxidative functionalisation of SuperQuat enamides: Asymmetric synthesis of homochiral 1,2 diols

Abstract:: Homochiral (E)-enamides derived from (S)-4-phenyl-5,5-dimethyl-oxazolidin-2-one undergo highly diastereoselective epoxidation upon treatment with dimethyldioxirane (DMDO). Treatment with m-chloroperbenzoic acid (MCPBA) produces syn-(4S, 1′R,2′)-1′ -acyloxy-2′-hydroxy derivatives with high diastereoselectivity, consistent with a mechanism involving initial epoxidation and subsequent in situ S N1 type epoxide opening and trapping with m-chlorobenzoic acid. Reductive clea...
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Publication status:: Published

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APA Style

Davies, S., Key, M. S., Rodriguez-Solla, H., Sanganee, H., Savory, E., & Smith, A. (2003). Oxidative functionalisation of SuperQuat enamides: Asymmetric synthesis of homochiral 1,2 diols. SYNLETT, 11, 1659–1662.

MLA Style

Davies, S., et al. “Oxidative Functionalisation of SuperQuat Enamides: Asymmetric Synthesis of Homochiral 1,2 Diols.” SYNLETT, no. 11, 2003, pp. 1659–62.

Chicago Style

Davies, S, MS Key, H Rodriguez-Solla, H Sanganee, E Savory, and A Smith. 2003. “Oxidative Functionalisation of SuperQuat Enamides: Asymmetric Synthesis of Homochiral 1,2 Diols.” SYNLETT, no. 11: 1659–62.
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Publisher copy:: 10.1055/s-2003-41425

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+ Davies, S More by this author

Institution:

University of Oxford

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MPLS

Department:

Chemistry

Sub department:

Organic Chemistry

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Author

+ Key, MS More by this author

Role:

Author

+ Rodriguez-Solla, H More by this author

Role:

Author

+ Sanganee, H More by this author

Role:

Author

+ Savory, E More by this author

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Bibliographic Details

Journal:: SYNLETT More from this journal
Issue:: 11
Pages:: 1659-1662
Publication date:: 2003-09-02
DOI:: 10.1055/s-2003-41425
EISSN:: 1437-2096
ISSN:: 0936-5214

Item Description

Language:: English
Keywords:: homochiral 1,2-diols

SuperQuat enarnides

asymmetric synthesis
Pubs id:: pubs:110583
UUID:: uuid:e237b8b3-019f-46ad-b63e-1470084d1f79
Local pid:: pubs:110583
Source identifiers:: 110583
Deposit date:: 2012-12-19

Terms of use

Copyright date:: 2003

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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