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Stereospecific Coupling of Alcohols and Carbanion Nucleophiles through a Circular P(V) Activation Manifold

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide We report a method for the stereospecific construction of sp 3 –sp 3 carbon–carbon bonds using alcohols and carbanion nucleophiles. The process is based on a circular phosphorus(V) manifold which starts and ends with triphenylphosphine oxide. The redox neutral approach eliminates the need for hazardous diazodicarboxylate oxidants and allows for recovery and recycling of triphenylphosphine oxide. Alcohol activation is achieved in situ through formation of alkoxyphosphonium triflates, which are kinetically stable, and undergo coupling with exogenous carbanion nucleophiles. In this manner, a range of alcohols undergo deoxyalkylation with inversion of configuration in moderate to excellent yield.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c04289

Authors: Isabel L. Wood, Stephen P. Argent, Ross M. Denton

Institution: University of Nottingham

Language: English

Topic: Phosphorus compounds and reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: Engineering and Physical Sciences Research Council