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J Am Chem Soc. 2005 May 25;127(20):7320-1.

Highly enantioselective and regioselective nickel-catalyzed coupling of allenes, aldehydes, and silanes.

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1
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, 02139, USA.

Abstract

A complex derived from Ni(cod)2 and NHC-IPr catalyzes a three-component coupling reaction involving allenes, aldehydes, and organosilanes and transfers the axial chirality of the allene to a stereogenic center in the product with very high fidelity. An unexpected regioselectivity is observed; favored are allylic rather than homoallylic alcohol derivatives, corresponding to the unusual process of coupling two electrophilic atoms: the allene sp and aldehyde carbon atoms. In all cases, high enantioselectivity, high Z/E selectivity, and, with differentially substituted allenes, high site selectivity are observed. This transformation represents the first enantioselective multicomponent coupling process of allenes.

PMID:
15898774
DOI:
10.1021/ja0521831
[Indexed for MEDLINE]
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