One-Pot Conversion of Aldehydes and Ketones into 1-Substituted and 1,4-Disubstituted 1,3-Enynes

被引：11
|
作者：
Cabezas, Jorge A. [1 ]
Poveda, Rebeca R. [1 ]
Brenes, Jose A. [1 ]
机构：
[1] Univ Costa Rica, Escuela Quim, San Jose 2060, Costa Rica
来源：
SYNTHESIS-STUTTGART | 2018年 / 50卷 / 17期
关键词：
1,3-dilithiopropyne; lithium acetylides; 1,3-enynes; palladium catalysis; cross-coupling; propargylation; STEREOSELECTIVE-SYNTHESIS; ANTITUMOR ANTIBIOTICS; CATALYZED SYNTHESIS; ALGAL CAROTENOIDS; CONJUGATED ENYNES; PHORBASIDES-A; SEX-PHEROMONE; CHEMISTRY; ACCESS; NEOCARZINOSTATIN;
D O I：
10.1055/s-0037-1610197
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Sequential treatment of 2,3-dichioropropene with magnesium and n-BuLi generates the operational equivalent of 1 ,3-dilithiopropyne, which upon treatment with aldehydes or ketones, produces the corresponding alkoxy lithium acetylide intermediates. Reaction of this alkoxide with tosyl chloride, and t-BuLi produces 1-substituted, or 1,1 - disubstituted 1,3-enynes in a one-pot reaction. When this lithium acetylide intermediates, obtained by this procedure, were used to perform palladium-catalyzed cross-coupling reactions, followed by addition of thionyl chloride and pyridine, 1,4-disubstituted or 1,1,4-trisubstituted 1,3-enynes were obtained in a one-pot protocol.
引用
收藏
页码：3307 / 3321
页数：15
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