手性羰基叶立德与芳基联烯的对映选择性环加成反应使用 Rh2(S-TCPTTL)4。

Enantioselective cycloaddition of carbonyl ylides with arylallenes using Rh2(S-TCPTTL)4.

机构信息

Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.

出版信息

Org Biomol Chem. 2013 Aug 28;11(32):5374-82. doi: 10.1039/c3ob41236a.

PMID:23852012

Abstract

The first catalytic asymmetric carbonyl ylide cycloaddition with arylallenes is described. With dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh2(S-TCPTTL)4, the cycloaddition of carbonyl ylides derived from diazoketoesters with arylallenes proceeded in a fully chemo- and regioselective manner to give highly functionalized 8-oxabicyclo[3.2.1]octanes with up to 99% ee and perfect exo diastereoselectivity.

摘要

首次描述了芳基联烯的首例催化不对称羰基叶立德环加成反应。使用二钌 (II) 四[N-四氯邻苯二甲酰基-(S)-叔亮氨酸]，Rh2(S-TCPTTL)4，重氮酮酯衍生的羰基叶立德与芳基联烯的环加成以完全化学和区域选择性的方式进行，得到高官能化的 8-氧杂双环[3.2.1]辛烷，ee 值高达 99%，外消旋选择性极好。