期刊
ACS CATALYSIS
卷 2, 期 8, 页码 1661-1666出版社
AMER CHEMICAL SOC
DOI: 10.1021/cs300290j
关键词
asymmetric catalysis; bifunctional; hydrogen bonding silanol; aldol; oxindole
资金
- University of California, Davis
- NSF [CHE-0847358]
- 3M Corporation
- Direct For Mathematical & Physical Scien [0847358] Funding Source: National Science Foundation
- Division Of Chemistry [0847358] Funding Source: National Science Foundation
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.
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