anti-1,2-Diols via Ni-Catalyzed Reductive Coupling of Alkynes and α-Oxyaldehydes

Ni-catalyzed reductive coupling of aryl alkynes (1) and enantiomerically enriched α-oxyaldehydes (2) afford differentiated anti-1,2-diols (3) with high diastereoselectivity and regioselectivity, despite the fact that the methoxymethyl (MOM) and para-methoxybenzyl (PMB) protective groups typically fa...

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Bibliographic Details
Published in:Organic letters 2005-07, Vol.7 (14), p.2937-2940
Main Authors: Luanphaisarnnont, Torsak, Ndubaku, Chudi O, Jamison, Timothy F
Format: Article
Language:English
Subjects:
Alcohols - chemical synthesis
Alcohols - chemistry
Aldehydes - chemistry
Alkynes - chemistry
Catalysis
Molecular Structure
Nickel - chemistry
Oxidation-Reduction
Stereoisomerism
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Summary:Ni-catalyzed reductive coupling of aryl alkynes (1) and enantiomerically enriched α-oxyaldehydes (2) afford differentiated anti-1,2-diols (3) with high diastereoselectivity and regioselectivity, despite the fact that the methoxymethyl (MOM) and para-methoxybenzyl (PMB) protective groups typically favor syn-1,2-diol formation in carbonyl addition reactions of this family of aldehydes.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol050881k