LETTER	Synlett 2006: 1879-1882   DOI: 10.1055/s-2006-947354
© Georg Thieme Verlag Stuttgart · New York
Remarkably Chemoselective Reduction of Unmodified Baylis-Hillman Adducts by InCl3/NaBH4: Application to the Stereoselective Synthesis of Trisubstituted Alkenones Including Two Alarm Pheromones [1]
Biswanath Das*, Joydeep Banerjee, Nikhil Chowdhury, Anjoy Majhi, Harish Holla
Organic Chemistry Division I, Indian Institute of Chemical Technology, Hyderabad, 500 007, India Fax: +91(40)7160512; e-Mail: biswanathdas@yahoo.com;
Received 30 March 2006

Abstract

A novel, convenient and solely stereoselective synthesis of trisubstituted E-alkenones has been achieved by InCl₃/NaBH₄ 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.

Key words

unmodified Baylis-Hillman adduct - chemoselectivity - stereoselectivity - α,β-unsaturated ketones - insects' pheromones

1

IICT communication No. 060622. Part 80 in the series ‘Studies on Novel Synthetic Methodologies'.