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Asymmetric Diels–Alder reactions of optically active oxazolidinone-derived vinylsulfonamides

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
12
Issue
13
Identifiers
DOI: 10.1016/s0957-4166(01)00320-2

Abstract

Abstract Chiral vinylsulfonamides bearing an oxazolidin-2-one moiety derived from ( R)-2-phenylglycinol and (1 R,2 S)-norephedrine have been employed as dienophiles in asymmetric Diels–Alder reactions at normal pressure affording d.e.s of up to 99% when EtAlCl 2 or Et 2AlCl were employed as Lewis acids. Theoretical calculations justify the observed enantio- and diastereoselectivity.

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