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

Richmond Lee; Fangrui Zhong; Bin Zheng; Yuezhong Meng; Yixin Lu; Kuo-Wei Huang

doi:10.1039/c3ob40144h

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

Richmond Lee, Fangrui Zhong, Bin Zheng, Yuezhong Meng, Yixin Lu, Kuo-Wei Huang

Research output: Contribution to journal › Article › peer-review

38 Scopus citations

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.

Original language	English (US)
Pages (from-to)	4818
Journal	Organic & Biomolecular Chemistry
Volume	11
Issue number	29
DOIs	https://doi.org/10.1039/c3ob40144h
State	Published - 2013

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Physical and Theoretical Chemistry

Access to Document

10.1039/c3ob40144h

Cite this

@article{3267308827fd41c580a842bbe580ae1b,

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

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. {\textcopyright} 2013 The Royal Society of Chemistry.",

author = "Richmond Lee and Fangrui Zhong and Bin Zheng and Yuezhong Meng and Yixin Lu and Kuo-Wei Huang",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: 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.",

year = "2013",

doi = "10.1039/c3ob40144h",

language = "English (US)",

volume = "11",

pages = "4818",

journal = "Organic & Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "29",

}

TY - JOUR

T1 - The origin of enantioselectivity in the l-threonine-derived phosphine-sulfonamide catalyzed aza-Morita-Baylis-Hillman reaction: Effects of the intramolecular hydrogen bonding

AU - Lee, Richmond

AU - Zhong, Fangrui

AU - Zheng, Bin

AU - Meng, Yuezhong

AU - Lu, Yixin

AU - Huang, Kuo-Wei

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: 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.

PY - 2013

Y1 - 2013

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/562513

UR - http://xlink.rsc.org/?DOI=c3ob40144h

UR - http://www.scopus.com/inward/record.url?scp=84880100870&partnerID=8YFLogxK

U2 - 10.1039/c3ob40144h

DO - 10.1039/c3ob40144h

M3 - Article

C2 - 23774825

SN - 1477-0520

VL - 11

SP - 4818

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 29

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this