[2,3]-Sigmatropic Rearrangements of 2-Phosphineborane 2-Propen-1-ols: Rapid Access to Enantioenriched Diphosphine Monoxide Derivatives
详细信息 查看全文
- 作者：Carl A. Busacca ; Bo Qu ; Elisa Farber ; Nizar Haddad ; Nicole Gr臎t ; Anjan K. Saha ; Magnus C. Eriksson ; Jiang-Ping Wu ; Keith R. Fandrick ; Steve Han ; Nelu Grinberg ; Shengli Ma ; Heewon Lee ; Zhibin Li ; Michael Spinelli ; Austin Gold ; Zhuzhu Wang ; Guijun Wang ; Peter Wipf ; Chris H. Senanayake
- 刊名：Organic Letters
- 出版年：2013
- 出版时间：March 1, 2013
- 年：2013
- 卷：15
- 期：5
- 页码：1136-1139
- 全文大小：267K
- 年卷期：v.15,no.5(March 1, 2013)
- ISSN：1523-7052
文摘
Hydrophosphination of secondary propargylic alcohols generates phosphine-containing allylic alcohols that undergo facile [2,3]-sigmatropic rearrangements with chlorophosphines, furnishing highly enantioenriched, crystalline diphosphine monoxides. The configuration at the newly formed stereocenter is opposite to that expected based on prior studies, and an ab initio computational evaluation of the possible transition states was performed to help explain the stereochemical course of the reaction.