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The origin of enantioselectivity in the l-threonine-derived phosphine-sulfonamide catalyzed aza-Morita-Baylis-Hillman reaction: Effects of the intramolecular hydrogen bonding

Journal Article


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.

Publication Date


  • 2013

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 and Biomolecular Chemistry, 11(29), 4818-4824. doi:10.1039/c3ob40144h

Scopus Eid


  • 2-s2.0-84880100870

Start Page


  • 4818

End Page


  • 4824

Volume


  • 11

Issue


  • 29

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.

Publication Date


  • 2013

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 and Biomolecular Chemistry, 11(29), 4818-4824. doi:10.1039/c3ob40144h

Scopus Eid


  • 2-s2.0-84880100870

Start Page


  • 4818

End Page


  • 4824

Volume


  • 11

Issue


  • 29