[1,2]‐Phospha‐Brook Rearrangement as Tool for Generation of Anionic Nucleophiles in Addition Reactions under Brønsted Base Catalysis

The [1,2]-phospha-Brook rearrangement involves the migration of the dialkoxyphosphoryl moiety of the alkoxide of an α-hydroxyphosphonate from carbon to oxygen to generate an α-oxygenated carbanion. This review article focused on the recent development of the Brønsted base-catalyzed addition reactions in which the [1,2]-phospha-Brook rearrangement is utilized for the generation of carbon-based anionic nucleophiles.

Abstract

The [1,2]-phospha-Brook rearrangement involves the migration of the dialkoxyphosphoryl moiety of the alkoxide of an α-hydroxyphosphonate from carbon to oxygen to generate an α-oxygenated carbanion. The alkoxide that is the precursor for the rearrangement is easily accessible by the deprotonation of α-hydroxyphosphonates or the addition of the anion of secondary phosphites to carbonyl compounds under the influence of a Brønsted base. This review article summarized recent development of the Brønsted base-catalyzed addition reactions in which the [1,2]-phospha-Brook rearrangement is utilized for the generation of carbon-based anionic nucleophiles.

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