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通过有机硅烷导向的不对称炔烃-烯烃还原偶联和环化序列,实现功能化碳环的发散合成。

Divergent synthesis of functionalized carbocycles through organosilane-directed asymmetric alkyne-alkene reductive coupling and annulation sequence.

机构信息

Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, Boston, Massachusetts 02215, USA.

出版信息

J Am Chem Soc. 2012 Nov 7;134(44):18440-6. doi: 10.1021/ja3083945. Epub 2012 Oct 23.

Abstract

An organosilane-directed alkyne-alkene reductive coupling of readily available propargylsilanes is used to access densely functionalized chiral allylsilanes. The divergent reactivity of the allylsilanes can be controlled to afford a range of novel carbocyclic ring systems through an intramolecular allylation, [3+2] annulation, and Sakurai-like homodimerization.

摘要

一种有机硅烷导向的炔烃-烯烃还原偶联反应,可用于获得易于获得的丙炔基硅烷,从而得到官能化的手性烯丙基硅烷。通过分子内烯丙基化、[3+2]环加成和 Sakurai 型同二聚化反应,可以控制烯丙基硅烷的发散反应性,从而得到一系列新型碳环体系。

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