4.4 Article

Asymmetric hetero-Diels-Alder reaction of chiral pinanediol 1,3-dienylboronates with azo-compounds

Journal

TETRAHEDRON
Volume 57, Issue 12, Pages 2305-2309

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(01)00110-7

Keywords

Diels-Alder reaction; azo-compounds; vinylboronic ester

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The asymmetric hetero-Diels-Alder reaction of 1,3-dienylboronates 1a and 1b with ate-compounds was investigated. The inductive effect of the methyl in 1,3-dienylboronate 1a resulted in an unusual product 7, while the normal cycloadduct 8 could be obtained as the single stereoisomer by using 1,3-dienylboronate 1b. (C) 2001 Elsevier Science Ltd. All rights reserved.

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