Organic letters

Iron-Promoted Elimination of β-Thioalkoxy Alcohols. Olefination by Coupling of a Carbonyl Group with a Dithioacetal

LF Huang, CW Chen, TY Luh

Index: Huang, Li-Fu; Chen, Chih-Wei; Luh, Tien-Yau Organic Letters, 2007 , vol. 9, # 18 p. 3663 - 3665

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Citation Number: 7

Abstract

Treatment of propargylic dithiolanes with n BuLi followed by a carbonyl electrophile yields the corresponding propargylic dithioacetals. Upon treatment with 1 equiv of Fe (acac) 3 and excess MeMgI, elimination of SR and OH moieties from 8 affords the corresponding olefins in satisfactory yield. Benzylic dithioacetals behave similarly. The reaction can be considered an alternative of McMurry coupling of two different carbonyl equivalents.

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