Please use this identifier to cite or link to this item: https://doi.org/10.1039/c3ob40144h
Title: The origin of enantioselectivity in the l-threonine-derived phosphine-sulfonamide catalyzed aza-Morita-Baylis-Hillman reaction: Effects of the intramolecular hydrogen bonding
Authors: Lee, R.
Zhong, F.
Zheng, B.
Meng, Y.
Lu, Y. 
Huang, K.-W.
Issue Date: 7-Aug-2013
Citation: Lee, R., Zhong, F., Zheng, B., Meng, Y., Lu, Y., Huang, K.-W. (2013-08-07). The origin of enantioselectivity in the l-threonine-derived phosphine-sulfonamide catalyzed aza-Morita-Baylis-Hillman reaction: Effects of the intramolecular hydrogen bonding. Organic and Biomolecular Chemistry 11 (29) : 4818-4824. ScholarBank@NUS Repository. https://doi.org/10.1039/c3ob40144h
Abstract: 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⋯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. © 2013 The Royal Society of Chemistry.
Source Title: Organic and Biomolecular Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/77247
ISSN: 14770520
DOI: 10.1039/c3ob40144h
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