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. 2009 Dec 2;131(47):17074-5.
doi: 10.1021/ja909030c.

Palladium-catalyzed enantioselective addition of two distinct nucleophiles across alkenes capable of quinone methide formation

Katrina H Jensen  1 , Tejas P Pathak, Yang Zhang, Matthew S Sigman
Affiliations

Palladium-catalyzed enantioselective addition of two distinct nucleophiles across alkenes capable of quinone methide formation

Katrina H Jensen et al. J Am Chem Soc. .

Abstract

A sequential intramolecular-intermolecular enantioselective alkene difunctionalization reaction has been developed which is thought to proceed through Pd-catalyzed quinone methide formation. The synthesis of new chiral heterocyclic compounds with adjacent chiral centers is achieved in enantiomeric ratios up to 99:1 and diastereomeric ratios up to 10:1.

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Figures

Scheme 1
Scheme 1
Avoiding β-hydride elimination to develop Pd-catalyzed alkene difunctionalization reactions.
See this image and copyright information in PMC

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