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Greatly Enhanced Enantioselectivity by an Apparently Remote Steric Effect in the 1,1′-Binaphthyl-catalyzed Alkynylzinc Addition to Aldehydes by David Moore; Wei-Sheng Huang; Ming-Hua Xu; Lin Pu is a Chemistry article available to read on EtoBox.

What is Greatly Enhanced Enantioselectivity by an Apparently Remote Steric Effect in the 1,1′-Binaphthyl-catalyzed Alkynylzinc Addition to Aldehydes about?

An unusual steric effect in the binaphthyl-catalyzed asymmetric alkynylzinc addition to aldehydes is observed. Increasing the steric bulkiness at the para-position of the 3,3%-anisyl groups of the 1,1%-binaphthyl ligands, though apparently remote from the Lewis acid coordination sites, has greatly enhanced the enantioselectivity as well as catalytic activity. Propargyl alcohols with ees up to 92% have been produced from the reaction of a terminal alkyne with aromatic aldehydes by using the binaphthyl catalysts.

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Author

David Moore; Wei-Sheng Huang; Ming-Hua Xu; Lin Pu

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4039)

Published

2002

Language

EN

Field

Chemistry (Physical Sciences)