The phospha-Michael addition in organic synthesis

Phosphorus is essential for many reagents in organic synthesis, for ligands of late-transition metals and for phosphono-and phosphanylamino acids, the latter being important isosteres of amino acids. Similar to the Michaelis-Arbuzov and the Michaelis-Becker reaction the phospha-Michael addition, i.e. the addition of a phosphorus nucleophile to an acceptor-substituted alkene or alkyne, certainly represents one of the most versatile and powerful tools for the formation of P-C bonds since many different electrophiles and P nucleophiles can be combined with each other. This offers the possibility to access many diversely functionalised products. With this article, we try to give an instructive overview of this reaction. The outline of this review is supposed to be rather general and it is its goal to make the reader familiar with reactivity principles which are common to the different classes of electrophiles and/or P nucleophiles. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).