Pudovik reaction phosphorus nucleophile-carbonyl

If a nucleophilic addition at a carbonyl or imine carbon occurs, the product is still a phosphinate (from a phosphonous ester) or a phosphine oxide (from a phosphinous ester), but the reaction is commonly referred to as an Abramov or Pudovik reaction. An example of the Pudovik reaction is shown below (equation 16). Addition of the phosphorus nucleophile to the /3-carbon atom of an a, /3-unsaturated substrate (Michael addition) is commonly referred to as a hydrophosphinylation reaction. ... 

This reaction was first reported by Pudovik in 1950. It is a base-promoted nucleophilic addition of organophosphorus anion to alkenes or alkynes and is generally known as the Pudovik reaction. Occasionally, it is also referred to as the Pudovik addition. In addition, since Abramov discovered a similar addition reaction of phosphorus compounds to carbonyl compounds at the same time, the addition of organophosphorus compounds to activated unsaturated systems (e.g., alkenes, alkynes, ketones, aldehydes,and... 

Addition of Phosphorus Nucleophiles to Carbonyl Compounds Additions of dialkyl H-phosphonates (the Pudovik reaction) or trialkyl phosphites (the Abramov reaction) to carbonyl compounds constitute a convenient route to a-hydroxyphosphonates (Scheme 47.7). 

Asymmetric versions of these reactions, in which a stereocenter adjacent to the phosphorus is created in a controlled fashion, have been also developed " These rely either on diastereoselective reactions involving optically active starting material (a carbonyl compound or a phosphite) or on chiral catalysis. The Pudovik reaction with enantiopure nucleophiles containing a chiral phosphorus atom was found to occur without epimerization however, this feature has not been exploited yet in the synthesis of natural products or their analogs. ... 

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