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Asymmetric induction of four chiral centers by hetero Diels-Alder reaction of a chiral nitroso dienophile

✍ Scribed by Werbitzky, Oleg ;Klier, Konrad ;Felber, Helena

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
371 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The Diels‐Alder reaction of cis‐5,6‐diacetoxy‐1,3‐cyclohexadiene (1), which has a meso configuration, with the chiral nitroso dienophile 2 occurs with induction of four asymmetric centers in very high optical yield (ee = 94%) and leads to the dihydro oxazine 3 (89%). The influence of the reaction temperature on the asymmetric induction was investigated and the absolute configuration of the product determined. Reductive cleavage of the N  O bond of 3 presents a simple route to enantiomerically pure derivatives of (1__R__)‐conduramine A1 (82%).

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