Organic letters

Formal intermolecular 4+ 4 approach to cyclooctanoids: 4+ 3 capture of the Nazarov oxyallyl intermediate with simple 1, 3-dienes

Y Wang, BD Schill, AM Arif, FG West

Index: Wang, Yong; Schill, Brenden B.; Arif, Atta M.; West Organic Letters, 2003 , vol. 5, # 15 p. 2747 - 2750

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Citation Number: 72

Abstract

Simple 1, 4-dien-3-ones and 1, 3-dienes react in the presence of BF3⊙ OEt2 via a domino Nazarov electrocyclization/intermolecular [4+ 3]-cycloaddition sequence to furnish keto- bridged cyclooctenes in good yield. Most cases showed high diastereofacial selectivity and/or endo/exo selectivity, and surprising levels of regioselectivity were observed when isoprene was used as the diene partner.