Control of Olefin Geometry in Macrocyclic Ring-Closing Metathesis Using a Removable Silyl Group

被引:48
作者
Wang, Yikai [2 ]
Jimenez, Miguel [2 ]
Hansen, Anders S. [2 ]
Raiber, Eun-Ang [1 ]
Schreiber, Stuart L. [1 ,2 ]
Young, Damian W. [1 ]
机构
[1] Broad Inst Harvard & MIT, Chem Biol Program, Cambridge, MA 02142 USA
[2] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
关键词
DIVERSITY-ORIENTED SYNTHESIS; NITROGEN-CONTAINING HETEROCYCLES; NATURAL-PRODUCT SYNTHESIS; ALKYNE METATHESIS; CROSS-METATHESIS; SKELETAL DIVERSITY; COUPLING REACTION; SMALL-MOLECULE; RCM; ENYNE;
D O I
10.1021/ja202012s
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Introducing a silyl group at one of the internal olefin positions in diolefinic substrates results in E-selective olefin formation in macrocyclic ring-forming metathesis. The application of this method to a range of macrocyclic (E)-alkenylsiloxanes is described. Protodesilylation of alkenylsiloxane products yields novel Z-configured macrocycles.
引用
收藏
页码:9196 / 9199
页数:4
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