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. 2009 Dec 17;11(24):5734-7.
doi: 10.1021/ol902561r.

Cooperativity of regiochemistry control strategies in reductive couplings of propargyl alcohols and aldehydes

Hasnain A Malik  1 , Mani Raj Chaulagain, John Montgomery
Affiliations

Cooperativity of regiochemistry control strategies in reductive couplings of propargyl alcohols and aldehydes

Hasnain A Malik et al. Org Lett. .

Abstract

The nickel-catalyzed reductive coupling of propargyl alcohols and alkynes proceeds with excellent regiochemical control with an underlying electronic preference that can be supplemented by ligand size effects. The products obtained may be readily converted to substructures that are not directly available by an aldehyde-alkyne reductive coupling. A simple model for how steric and electronic factors are both important in governing regiochemistry in couplings of this type is presented, along with examples of how the effects can combine in either a constructive or destructive manner.

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Figures

Scheme 1
Scheme 1
Regiocontrol in Aldehyde-Alkyne Reductive Couplings.
Scheme 2
Scheme 2
Predictive Model for Regiocontrol.
Scheme 3
Scheme 3
Post-Coupling Manipulations.
See this image and copyright information in PMC

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