Tetrahedron

The role of proline in the asymmetric step of the woodward synthesis of erythromycin

C Agami, N Platzer, C Puchot, H Sevestre

Index: Agami; Platzer; Puchot; Sevestre Tetrahedron, 1987 ,  vol. 43,  # 6  p. 1091 - 1098

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Citation Number: 26

Abstract

Proline induces the enantioselectivity of the title reaction in an aldol reaction and not in a conjugate addition. This was demonstrated by the two following sets of experiments.(i) Recovered keto sulfides 4 and 5 did not show any optical activity when the racemic substrates were treated with (S)-proline; moreover (S)-proline was unable to induce chirality during the conjugate addition of thiophenol on cyclohexenone.(ii) Kinetic resolution of ...