Chemoselective reduction for different steroidal alpha, beta-unsaturated ketone into diene by using Luche reagent

Original Article

JOURNAL 1039

Organic Communications

VOLUME & ISSUE

Year: 2018 Issue: 4 October-December

PAGES

p.181 - 187

DOI ADDRESS

http://doi.org/10.25135/acg.oc.52.18.11.1039

STATISTICS

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AUTHORS

Khaled Shawakfeh
Raed Al-Zoubi
Walid Al-Jammal
Rasha Nuseir

GRAPHICAL ABSTRACT

ABSTRACT

The conjugate reduction of a,b-unsaturated carbonyl compounds remains an active area of organic synthesis. Our aim is to control the reducing potential and selectivity of conjugated enone reduction. After much experimentation, the best conditions found for maximum yield with chemo and regioselectivity were to employ 1 molar eqiv. of NaBH4 for each mole of substrate in methanol containing some cerium(III) chloride. Many enones were converted essentially quantitatively to the allylic alcohol at room temperature. Surprisingly, reduction of the enone system in compound 2 (1.0 mmol) with NaBH4 (1.0mmol) and cerium chloride (1.0 mmol) in MeOH gave compound 3, in which the enone system was reduced and the allylic alcohol dehydrated producing the diene system.

KEYWORDS

Regioslective
chemoselective
reduction
Luche reagent
diene
ketone