4.7 Article

Nickel-catalyzed enantioselective hydrovinylation of silyl-protected allylic alcohols: An efficient access to homoallylic alcohols with a chiral quaternary center

Journal

SCIENCE CHINA-CHEMISTRY
Volume 53, Issue 9, Pages 1899-1906

Publisher

SCIENCE PRESS
DOI: 10.1007/s11426-010-4036-6

Keywords

asymmetric hydrovinylation; chiral spiro phosphorus ligands; functionalized olefins; chiral quaternary center

Funding

  1. National Natural Science Foundation of China
  2. National Basic Research Program of China (973 Program) [2006CB806106, 2010CB833300]
  3. Ministry of Health [2009ZX09501-017]
  4. Ministry of Education of China [B06005]

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Asymmetric hydrovinylation of silyl-protected allylic alcohols catalyzed by nickel complexes of chiral spiro phosphoramidite ligands was developed. A series of homoallylic alcohols with a chiral quaternary center were produced in high yields (up to 97%) and high enantioselectivities (up to 95% ee). The reaction provides an efficient method for preparing bifunctional compounds with a chiral quaternary carbon center.

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