一锅法连续进行的铜催化硅烯醇醚还原反应和钯催化芳基化反应。

One-pot sequential Cu-catalyzed reduction and Pd-catalyzed arylation of silyl enol ethers.

作者信息

Chae Junghyun, Yun Jaesook, Buchwald Stephen L

机构信息

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

出版信息

Org Lett. 2004 Dec 23;6(26):4809-12. doi: 10.1021/ol048313c.

DOI:10.1021/ol048313c

PMID:15606072

Abstract

[reaction: see text] Enantiomerically enriched beta-substituted diphenylsilyl enol ethers, which can be prepared from Cu-catalyzed asymmetric conjugate reduction, are utilized in the Pd-catalyzed arylation of various aryl bromides. This new method provides a simple route to alpha-arylated cycloalkanones with excellent levels of enantiomeric and diastereomeric purity. The isolation of the intermediate, diphenylsilyl enol ethers is not necessary; the procedure can be carried out in one-pot.

摘要

[反应：见正文] 对映体富集的β-取代二苯基硅基烯醇醚可由铜催化的不对称共轭还原反应制备，用于钯催化的各种芳基溴的芳基化反应。这种新方法为制备对映体和非对映体纯度极高的α-芳基环烷酮提供了一条简便途径。无需分离中间体二苯基硅基烯醇醚；该过程可一锅法进行。