Remarkably Chemoselective Reduction of Unmodified Baylis-Hillman Adducts by InCl₃/NaBH₄: Application to the Stereoselective Synthesis of Trisubstituted Alkenones Including Two Alarm Pheromones

Biswanath Das*, Joydeep Banerjee, Nikhil Chowdhury, Anjoy Majhi, Harish Holla

*Organic Chemistry Divison I, Indian Institute of Chemical Technology, Hyderabad, Email: biswanathdasyahoo.com

B. Das, J. Banerjee, N. Chowdhury, A. Majhi, H. Holla, Synlett, 2006, 1879-1882.

DOI: 10.1055/s-2006-947354

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Abstract

A novel, convenient and stereoselective synthesis of trisubstituted E-alkenones has been achieved by InCl₃-mediated chemoselective reduction of Baylis-Hillman adducts with NaBH₄ as reductant.

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Key Words

Enones, Baylis-Hillman Adducts, Indium, Sodium Borohydride

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ID: J60-Y2006-4540