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阴离子控制的固态[2+2]环加成反应合成反式-3-(4-吡啶基)丙烯酸盐的环丁烷衍生物的立体选择性。

Anion-controlled stereoselective synthesis of cyclobutane derivatives by solid-state [2 + 2] cycloaddition reaction of the salts of trans-3-(4-pyridyl) acrylic acid.

机构信息

Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543.

出版信息

Org Lett. 2010 Jan 1;12(1):128-31. doi: 10.1021/ol9025233.

DOI:10.1021/ol9025233
PMID:19950977
Abstract

Two stereoisomers of cyclobutane derivatives with pyridyl and carboxylic acid functionalities have been stereoselectively synthesized by a solid-state photochemical [2 + 2] cycloaddition reaction in quantitative yields. The head-to-head and head-to-tail parallel orientations of the monomers, required to obtain these two isomers, have been controlled by the anions present in the salts. The photoinert behavior of these salts in solution signifies the importance of the solid-state synthesis of these cyclobutane derivatives.

摘要

两种具有吡啶基和羧酸官能团的环丁烷衍生物的对映异构体已通过固态光化学[2+2]环加成反应以定量产率立体选择性合成。获得这两种异构体所需的单体的头对头和头对尾平行取向通过盐中存在的阴离子控制。这些盐在溶液中的光惰性行为表明了这些环丁烷衍生物的固态合成的重要性。

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