Asymmetric Aldol Additions with a Titanium Enolate of N-Thioglycolyl Oxazolidinethione

Aurelio      Ortiz; Rocio      Sabala; Estibaliz      Sansinenea; Sylvain      Bernes

doi:10.2174/157017807782006380

Abstract

A titanium enolate of N-thioglycolyl oxazolidinethione has been prepared and used for the synthesis of "Evans" syn aldol adducts, in good yield and high selectivity. Removal of the chiral auxiliary was accomplished by reduction to the corresponding 1,3-diols or by preparation of Weinreb amides.

Keywords: Asymmetric aldol additions, titanium enolates, oxazolidinethione

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Letters in Organic Chemistry

Title: Asymmetric Aldol Additions with a Titanium Enolate of N-Thioglycolyl Oxazolidinethione

Volume: 4 Issue: 7

Author(s): Aurelio Ortiz, Rocio Sabala, Estibaliz Sansinenea and Sylvain Bernes

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Keywords: Asymmetric aldol additions, titanium enolates, oxazolidinethione

Abstract: A titanium enolate of N-thioglycolyl oxazolidinethione has been prepared and used for the synthesis of "Evans" syn aldol adducts, in good yield and high selectivity. Removal of the chiral auxiliary was accomplished by reduction to the corresponding 1,3-diols or by preparation of Weinreb amides.

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Ortiz Aurelio, Sabala Rocio, Sansinenea Estibaliz and Bernes Sylvain, Asymmetric Aldol Additions with a Titanium Enolate of N-Thioglycolyl Oxazolidinethione, Letters in Organic Chemistry 2007; 4 (7) . https://dx.doi.org/10.2174/157017807782006380