钛（IV）促进的向山羟醛-普林斯环化反应。

Titanium(IV)-promoted Mukaiyama aldol-Prins cyclizations.

作者信息

Patterson Brian, Marumoto Shinji, Rychnovsky Scott D

机构信息

Department of Chemistry, 516 Rowland Hall, University of California, Irvine, California 92697-2025, USA.

出版信息

Org Lett. 2003 Aug 21;5(17):3163-6. doi: 10.1021/ol035303n.

DOI:10.1021/ol035303n

PMID:12917007

Abstract

[reaction: see text] A new version of the Mukaiyama aldol-Prins (MAP) cyclization has been developed. Unsaturated enol ethers such as 3 were found to couple with aldehydes in the presence of TiBr(4) to give 4-bromotetrahydropyran products. This cascade reaction sequence leads to the formation of two new carbon-carbon bonds, a ring, and three new stereogenic centers. We expect this reaction to be a powerful new tool in synthesis.

摘要

[反应：见正文] 一种新型的向山羟醛-普林斯（MAP）环化反应已被开发出来。发现不饱和烯醇醚如3在TiBr(4)存在下能与醛发生偶联反应，生成4-溴四氢吡喃产物。这个串联反应序列导致形成两个新的碳-碳键、一个环和三个新的手性中心。我们预计该反应会成为合成领域一种强大的新工具。