Asymmetric hydroformylation and hydrocarboxylation of enamides. Synthesis of alanine and proline

Y Becker, A Eisenstadt, JK Stille

Index: Becker, Y.; Eisenstadt, A.; Stille, J. K. Journal of Organic Chemistry, 1980 , vol. 45, # 11 p. 2145 - 2151

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Citation Number: 115

Abstract

Carbonyltris (tripheny1phosphine) hydridorhodium (1) catalyzed the hydroformylation of N- vinylimides in the presence of optically active 2, 3-O-isopropylidene-2, 3-dihydroxy-l, 4-bis (diphenylphosphino) butane (DIOP) or 2, 3-O-isopropylidene-2, 3-dihydroxy-l, 4-bis (5H- dibenzophospholyl) butane (DIPHOL) to afford optically active a-amido aldehydes. Linear disubstituted N-vinylimides or-amides reacted very sluggishly, while the cyclic N-acyl-2- ...