Michael Addition Reactions with 2-Coordinated Anisoles: Controlling the Stereochemistry of the Para and Benzylic Carbons
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- 作者：Philip L. Smith ; Joseph M. Keane ; Sarah E. Shankman ; Mahendra D. Chordia ; and W. Dean Harman
- 刊名：Journal of the American Chemical Society
- 出版年：2004
- 出版时间：December 1, 2004
- 年：2004
- 卷：126
- 期：47
- 页码：15543 - 15551
- 全文大小：140K
- 年卷期：v.126,no.47(December 1, 2004)
- ISSN：1520-5126
文摘
Several 
2-coordinated anisole complexes were treated with various Michael acceptors in thepresence of a Lewis or Br
nsted acid to generate stable 4H-anisolium complexes. These reactions werefound to proceed with high stereochemical control with predictable outcomes, provided that the moderateacid (NH2Ph2)OTf was used and the complex was dissolved in an acidic solution. The stereochemistry isshown to originate from an unexpectedly high preference for one coordination diastereomer of the anisolecomplex in the solid state and a Diels-Alder like transition state for the Michael reaction.
2-coordinated anisole complexes were treated with various Michael acceptors in thepresence of a Lewis or Brnsted acid to generate stable 4H-anisolium complexes. These reactions werefound to proceed with high stereochemical control with predictable outcomes, provided that the moderateacid (NH2Ph2)OTf was used and the complex was dissolved in an acidic solution. The stereochemistry isshown to originate from an unexpectedly high preference for one coordination diastereomer of the anisolecomplex in the solid state and a Diels-Alder like transition state for the Michael reaction.© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号 地址：北京市海淀区学院路29号 邮编：100083 电话：办公室：(+86 10)66554848；文献借阅、咨询服务、科技查新：66554700 |