The origin of enantioselectivity in the l-threonine-derived phosphine-sulfonamide catalyzed aza-Morita-Baylis-Hillman reaction: Effects of the intramolecular hydrogen bonding
Type
ArticleKAUST Department
Chemical Science ProgramHomogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2013Permanent link to this record
http://hdl.handle.net/10754/562513
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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.Citation
Lee, R., Zhong, F., Zheng, B., Meng, Y., Lu, Y., & Huang, K.-W. (2013). The origin of enantioselectivity in the l-threonine-derived phosphine–sulfonamide catalyzed aza-Morita–Baylis–Hillman reaction: effects of the intramolecular hydrogen bonding. Organic & Biomolecular Chemistry, 11(29), 4818. doi:10.1039/c3ob40144hSponsors
We are grateful for the generous financial support from King Abdullah University of Science and Technology to K.-W.H. and from the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-494-112) to Y. L.Publisher
Royal Society of Chemistry (RSC)Journal
Organic & Biomolecular ChemistryPubMed ID
23774825ae974a485f413a2113503eed53cd6c53
10.1039/c3ob40144h
Scopus Count
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