期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 11, 期 29, 页码 4818-4824出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob40144h
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资金
- King Abdullah University of Science and Technology
- National University of Singapore
- Ministry of Education (MOE) of Singapore [R-143-000-494-112]
L-Threonine-derived phosphine-sulfonamide 4 was identified as the most efficient catalyst to promote enantioselective aza-Morita-Baylis-Hillman (MBH) reactions, affording the desired aza-MBH adducts with excellent enantioselectivities. Density functional theory (DFT) studies were carried out to elucidate the origin of the observed enantioselectivity. The importance of the intramolecular N-H center dot center dot center dot O hydrogen-bonding interaction between the sulfonamide and enolate groups was identified to be crucial in inducing a high degree of stereochemical control in both the enolate addition to imine and the subsequent proton transfer step, affording aza-MBH reactions with excellent enantioselectivity.
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