Site- and Enantioselective Formation of Allene-Bearing Tertiary or Quaternary Carbon Stereogenic Centers through NHC-Cu-Catalyzed Allylic Substitution

Byunghyuck Jung and Amir H. Hoveyda *

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States, Email: amir.hoveydabc.edu

B. Jung, A. H. Hoveyda, J. Am. Chem. Soc., 2012, 134, 1490-1493.

DOI: 10.1021/ja211269w

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Abstract

Sulfonate-bearing chiral bidentate N-heterocyclic carbene (NHC) complexes of copper enable catalytic enantioselective allylic substitutions of allylic phosphonates with commercially available allenylboronic acid that result in addition of an allenyl group and formation of tertiary or quaternary C-C bonds in up to 95% yield, >98% S_N2′ selectivity, and 98% ee.

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Key Words

Allenes, 1,4-Dienes

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ID: J48-Y2012-0170