anti-1,2-diols via Ni-catalyzed reductive coupling of alkynes and α-oxyaldehydes

Torsak Luanphaisarnnont; Chudi O. Ndubaku; Timothy F. Jamison

doi:10.1021/ol050881k

anti-1,2-diols via Ni-catalyzed reductive coupling of alkynes and α-oxyaldehydes

Torsak Luanphaisarnnont
, Chudi O. Ndubaku
, Timothy F. Jamison

LIGO-Massachusetts Institute of Technology

Research output: Contribution to journal › Article › peer-review

65 Citations (Scopus)

Abstract

(Chemical Equation Presented) Ni-catalyzed reductive coupling of aryl alkynes (1) and enantiomerically enriched α-oxyaldehydes (2) afford differentiated anti-2,2-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.

Original language	English
Pages (from-to)	2937-2940
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	14
DOIs	https://doi.org/10.1021/ol050881k
Publication status	Published - 7 Jul 2005
Externally published	Yes

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title = "anti-1,2-diols via Ni-catalyzed reductive coupling of alkynes and α-oxyaldehydes",

abstract = "(Chemical Equation Presented) Ni-catalyzed reductive coupling of aryl alkynes (1) and enantiomerically enriched α-oxyaldehydes (2) afford differentiated anti-2,2-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.",

author = "Torsak Luanphaisarnnont and Ndubaku, \{Chudi O.\} and Jamison, \{Timothy F.\}",

year = "2005",

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doi = "10.1021/ol050881k",

language = "English",

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journal = "Organic Letters",

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T1 - anti-1,2-diols via Ni-catalyzed reductive coupling of alkynes and α-oxyaldehydes

AU - Luanphaisarnnont, Torsak

AU - Ndubaku, Chudi O.

AU - Jamison, Timothy F.

PY - 2005/7/7

Y1 - 2005/7/7

N2 - (Chemical Equation Presented) Ni-catalyzed reductive coupling of aryl alkynes (1) and enantiomerically enriched α-oxyaldehydes (2) afford differentiated anti-2,2-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.

AB - (Chemical Equation Presented) Ni-catalyzed reductive coupling of aryl alkynes (1) and enantiomerically enriched α-oxyaldehydes (2) afford differentiated anti-2,2-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.

UR - https://www.scopus.com/pages/publications/22244490357

U2 - 10.1021/ol050881k

DO - 10.1021/ol050881k

M3 - Article

C2 - 15987174

AN - SCOPUS:22244490357

SN - 1523-7060

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SP - 2937

EP - 2940

JO - Organic Letters

JF - Organic Letters

IS - 14

ER -

anti-1,2-diols via Ni-catalyzed reductive coupling of alkynes and α-oxyaldehydes

Abstract

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