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
Full Text: HTML
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.
Related Articles:
[Hayashi, Naoki; Kusano, Kazunao; Sekizawa, Shingo; Shibata, Ikuya; Yasuda, Makoto; Baba, Akio Chemical Communications, 2007 , # 46 p. 4913 - 4915]
[Firouzabadi, Habib; Iranpoor, Naser; Hazarkhani, Hassan; Karimi, Babak Synthetic Communications, 2003 , vol. 33, # 21 p. 3653 - 3660]
Synthese und Ringöffnung von hochsubstituierten 1, 1??Dichlor??und 1??Brom??1??fluorcyclopropanen
[Anke, Lutz; Reinhard, Detlef; Weyerstahl, Peter Liebigs Annalen der Chemie, 1981 , # 4 p. 591 - 602]
[Ando,W. et al. Journal of the American Chemical Society, 1977 , vol. 99, p. 6995 - 6999]
A facile two-step synthesis of 2-arylbenzofurans based on the selective cross McMurry couplings
[Duan, Xin-Fang; Zeng, Jing; Lue, Jia-Wei; Zhang, Zhan-Bin Journal of Organic Chemistry, 2006 , vol. 71, # 26 p. 9873 - 9876]