Enantiocontrol with a Hydrogen-bond Directing Pyrrolidinylsilanol Catalyst
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- 作者：Taewoo Min ; James C. Fettinger ; Annaliese K. Franz
- 刊名：ACS Catalysis
- 出版年：2012
- 出版时间：August 3, 2012
- 年：2012
- 卷：2
- 期：8
- 页码：1661-1666
- 全文大小：370K
- 年卷期：v.2,no.8(August 3, 2012)
- ISSN：2155-5435
文摘
A new bifunctional catalyst containing a silanol group has been designed and synthesized with high enantioselectivity in three steps. The hydrogen-bonding properties of this pyrrolidinylsilanol have been investigated using NMR binding studies and electrospray ionization mass spectrometry (ESI-MS) analysis. The ability of the silanol group to activate an electrophile and afford enantiocontrol through hydrogen-bond directing effects has been demonstrated using an enantioselective aldol reaction with isatin and acetaldehyde, affording up to 88% ee.