SYNTHESIS OF SECONDARY E-ALLYLAMINES AND BETA-AMINOPHOSPHORYLATED COMPOUNDS FROM BETA-FUNCTIONALIZED ENAMINES DERIVED FROM PHOSPHONIUM SALTS, PHOSPHINE OXIDES AND PHOSPHONATES

A simple and stereoselective synthesis of secondary E-allylamines 1 an d 20 from functionalized enamines derived from phosphine oxides 8, pho sphonium salts 11 and phosphonates 12 is reported. Phosphorus compound s 8, 11 and 12 are obtained by amine addition to phosphorylated allene s 7, 10 and phosphonium salts 9. Reduction of enamines 8 and 12 with h ydrides leads to the formation of beta-amino phosphine oxides 13 and p hosphonates 14. Allylamines 1, 20 and beta-aminophosphorylated derivat ives 13 and 14 can also be obtained in ''one pot'' reaction from allen es 7, 10 and phosphonium salts 9 without the isolation and purificatio n of enamines 8, 11 and 12. Copyright (C) 1996 Elsevier Science Ltd.