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Highly Enantioselective Darzens Reaction of a Camphor-Derived Sulfonium Amide to Give Glycidic Amides and Their Applications in Synthesis

Varinder K. Aggarwal,* George Hynd, Willy Picoul and Jean-Luc Vasse

*School of Chemistry, Bristol University, Cantock's Close, Bristol, BS8 1TS UK, Email: v.aggarwalbristol.ac.uk

V. K. Aggarwal, G. Hynd, W. Picoul, J.-L. Vasse, J. Am. Chem. Soc., 2002, 124, 9964-9965.

DOI: 10.1021/ja0272540 (free Supporting Information)



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Abstract

A camphor-derived amide-stabilized ylide reacts with aldehydes at -50C in ethanol to give glycidic amides in one step with up to 99% ee and complete diastereoselectivity. Further transformations of epoxyamides were investigated.


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Highly Enantioselective Synthesis of Glycidic Amides Using Camphor-Derived Sulfonium Salts. Mechanism and Applications in Synthesis

V. K. Aggarwal, J. P. H. Charmant,D. Fuentes,J. N. Harvey, G. Hynd, D. Ohara,W. Picoul, R. Robiette, C. Smith,J.-L. Vasse, C. L. Winn, J. Am. Chem. Soc. 2006, 128, 2105-2114. DOI: 10.1021/ja0568345


Key Words

Epoxides, Darzens Condensation


ID: J48-Y2002-1740