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Site- And Enantioselective Formation of Allene-Bearing Tertiary or Quaternary Carbon Stereogenic Centers Through NHC-Cu-catalyzed Allylic Substitution

Site- And Enantioselective Formation of Allene-Bearing Tertiary or Quaternary Carbon Stereogenic Centers Through NHC-Cu-catalyzed Allylic Substitution

Byunghyuck Jung, Amir H Hoveyda

J Am Chem Soc. 2012 Jan 25;134(3):1490-3.

PMID: 22214185

Abstract:

Catalytic enantioselective allylic substitutions that result in addition of an allenyl group (<2% propargyl addition) and formation of tertiary or quaternary C-C bonds are described. Commercially available allenylboronic acid pinacol ester is used. Reactions are promoted by a 5.0-10 mol % loading of sulfonate-bearing chiral bidentate N-heterocyclic carbene (NHC) complexes of copper, which exhibit the unique ability to furnish chiral products arising from the S(N)2' mode of addition. Allenyl-containing products are generated in up to 95% yield, >98% S(N)2' selectivity, and 99:1 enantiomeric ratio (er). Site-selective NHC-Cu-catalyzed hydroboration of enantiomerically enriched allenes and conversion to the corresponding β-vinyl ketones demonstrates the method's utility.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP865350170	Allenylboronic acid pinacol ester		865350-17-0	Price

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