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

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. Theo...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2001-07, Vol.12 (13), p.1811-1815
Main Authors: Bernabeu, M.Carmen, Chinchilla, Rafael, Falvello, Larry R., Nájera, Carmen
Format: Article
Language:English
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Summary: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. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(01)00320-2