Synlett

Remarkably chemoselective reduction of unmodified baylis-hillman adducts by InCl3/NaBH4: Application to the stereoselective synthesis of trisubstituted alkenones …

B Das, J Banerjee, N Chowdhury, A Majhi, H Holla

Index: Das, Biswanath; Banerjee, Joydeep; Chowdhury, Nikhil; Majhi, Anjoy; Holla, Harish Synlett, 2006 , # 12 p. 1879 - 1882

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Citation Number: 6

Abstract

Abstract A novel, convenient and solely stereoselective synthesis of trisubstituted E- alkenones has been achieved by InCl 3/NaBH 4 mediated chemoselective reduction of unmodified Baylis-Hillman adducts derived from vinyl ketones and cycloalkenones for the first time. The efficiency of this methodology in the practical synthesis of (S)-(+)-manicone and (S)-(+)-normanicone, two alarm pheromones of Manica ants, has been demonstrated.