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

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.

SUBMITTER: Malik HA

PROVIDER: S-EPMC2800991 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature

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

Malik Hasnain A HA Chaulagain Mani Raj MR Montgomery John J

Organic letters 20091201 24

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 e ...[more]

PMID: 19919081

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