4.7 Article

A Spirocyclic Chiral Borate for Catalytic Enantioselective Nozaki-Hiyama Allylation of Ketones

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 18, Pages 3089-3095

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900595

Keywords

aminoborates; bipyridyls; chromium catalysts; Nozaki-Hiyama allylation; spirocyclic borates

Funding

  1. National Science Council of the Republic of China [NSC 96-2811M-259-001, NSC 97-2113M-259-002-MY3]

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A new class of chiral spirocyclic borate ligands 5a-d with a rigid borocycle has been developed. The catalyst formed from chromium(II)-5a promotes the highly efficient enantioselective Nozaki-Hiyama allylation of alkyl and aryl ketones using allyl bromide. ne scope of the present method is shown to be wide, and it affords an efficient access to chiral tertiary homoallylic alcohols.

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