Diastereoselective Synthesis of α-Stabilized Phosphorus Ylides via a Four-Component Reaction

Abstract

Functionalized and α-stabilized derivatives of dialkyl 2-{1-[(alkylamino)carbonyl]-2-oxopropyl}-3-(1,1,1-triphenyl-λ⁵-phos­phanylidene)succinate were obtained in excellent yields from the reaction between primary amines, diketene, and dialkyl acetylenedicarboxylate in the presence of triphenylphosphine. Not only the reaction is diastereoselective but also the formed diasteromer has two rotamers that are in equilibrium with each other. ^¹H, ^¹³C, and ^³¹P NMR showed only one of the two rotamers and thus conversion of Z-isomer into another is negligible at room temperature.

Key words

α-stabilized phosphorus ylide - triphenylphosphine - diketene - dialkyl acetylenedicarboxylate - multicomponent reaction - diastereoselective reaction

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CCDC 695672 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: [phone]; E-mail: mailto:[e-mail]].