Phosphonamide-Stabilized Anions

Denmark has also investigated the carbanion accelerated Claisen rearrangement of allyl vinyl ethers with cydic phosphonamides as carbanion-stabihzing groups [78], because phosphonamide allyl anion is well established and has potential for chiral modification. 

1 Wipf, P. In Comprehensive Organic Synthesis 1991 Trost, B. Fleming, I. (eds.) Pergamon Press, New York, Vol. 5, p. 827. 

11 Mandai, X Matsumoto, S. Kohama, M. Kawada, M. Tsuji, J. Saito, S.  

38 Lubineau, A. Auge, J. Bellanger, N. Caillebourdin, S. Tetrahedron Lett. 1990, 31,4117. 

46 Hikota, M. Sakurai, Y Horita, K. Yonemitsu, O. Tetrahedron Lett. 1990, 31, 6367. 

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Phosphonamide-stabilized allylic anions react y-selectively and serve as homocnolate reagents86 in the reaction with aldehydes only moderate simple diastereoselectivity is observed. 

Cyclic phosphonamide a-carbanions are excellent olefination reagents particularly useful for enolizable carbonyl compounds. P-stabilized allyl anions have found application as Michael donors. " ... 

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