Hydrophosphination of Propargylic Alcohols and Amines with Phosphine Boranes
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- 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 ; 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：1132-1135
- 全文大小：239K
- 年卷期：v.15,no.5(March 1, 2013)
- ISSN：1523-7052
文摘
The first uncatalyzed hydrophosphinations of propargylic amines and alcohols with phosphine鈥?borane complexes are described. The reactions proceed at ambient temperature or below without the use of protecting groups or the need to handle pyrophoric secondary phosphines, furnishing air-stable phosphineborane鈥揳mines and alcohols in good yields. Utilization of chiral propargylic substrates and unsymmetrical secondary phosphineboranes leads to diastereomeric P-chiral products that can be separated by fractional crystallization or chromatography. Initial applications of these new P鈥揦 species to asymmetric catalysis are detailed.