DEVELOPMENT OF A TITANOCENE-CATALYZED ENYNE CYCLIZATION ISOCYANIDE INSERTION REACTION
DEVELOPMENT OF A TITANOCENE-CATALYZED ENYNE CYCLIZATION ISOCYANIDE INSERTION REACTION
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DOI：
10.1021/ja00098a020
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发表时间：
1994-09-21
影响因子：
15
通讯作者：
BUCHWALD, SL
中科院分区：
文献类型：
--
作者：
BERK, SC;GROSSMAN, RB;BUCHWALD, SL
报道了第一个早期过渡金属催化的烯炔环化反应。该体系在硅氰化物存在下，通过使用10mol%的Cp(2)Ti(PME(3))(2)将烯炔底物转化为双环亚胺环戊烯。随后的水解制得相应的双环环戊酮，总收率很高。该环化反应对醚、胺和酯等极性官能团是容忍的，与某些手性烯炔底物是非对映选择性的。
The first early transition metal-catalyzed enyne cyclization reaction is described. The system converts enyne substrates to bicyclic iminocyclopentenes through the use of 10 mol % of Cp(2)Ti(PMe(3))(2) in the presence of a silyl cyanide. Subsequent hydrolysis produces the corresponding bicyclic cyclopentenones in good overall yield. The cyclization reaction is tolerant of polar functional groups such as ethers, amines, and esters and is diastereoselective with certain chiral enyne substrates.