Isothiourea-catalyzed formal enantioselective conjugate addition of benzophenone imines to ß-fluorinated a,ß-unsaturated esters

Jerson Lapetaje; Claire M. Young; Chang Shu; Andrew D. Smith

doi:10.1039/D2CC01936A

Isothiourea-catalyzed formal enantioselective conjugate addition of benzophenone imines to ß-fluorinated a,ß-unsaturated esters

Jerson Lapetaje, Claire M. Young, Chang Shu, Andrew D. Smith^*

^*Corresponding author for this work

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

3 Citations (Scopus)

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Abstract

The isothiourea-catalyzed formal enantioselective conjugate addition of 2-hydroxybenzophenone imine derivatives to α,β-unsaturated para-nitrophenyl esters has been developed. Investigations of the scope and limitations of this procedure showed that β-electron withdrawing substituents within the α,β-unsaturated ester component was necessary for good product yield, giving rise to a range of β-imino ester and amide derivatives in moderate to good isolated yields with excellent enantioselectivity (20 examples, up to 81% yield and 97:3 er).

Original language	English
Pages (from-to)	6886-6889
Number of pages	4
Journal	Chemical Communications
Volume	58
Issue number	49
Early online date	20 May 2022
DOIs	https://doi.org/10.1039/D2CC01936A
Publication status	Published - 21 Jun 2022

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10.1039/D2CC01936ALicence: CC BY

Lapetaje_2022_ChemComm_Isothiourea_CC
Copyright © The Author(s). Open Access Article. This article is licensed under aCreative Commons Attribution 3.0 Unported Licence.
Final published version, 3.5 MBLicence: CC BY

Newton Fellowship Prof A Smith: Catalytic Enantioselective Synthesis of N-heterocycles using Lewis Base Catalysis
Smith, A. D. (PI)
The Royal Society
8/02/17 → 7/02/19
Project: Fellowship

data underpinning "Isothiourea-Catalyzed Enantioselective Conjugate Addition of Benzophenone Imine Derivatives to α,β-Unsaturated Esters"
Smith, A. D. (Creator), Lapetaje, J. (Owner), Young, C. M. (Owner) & Shu, C. (Owner), University of St Andrews, 24 May 2022
DOI: 10.17630/fb29b2d4-41d4-4143-a19b-5f59cb71447a
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@article{446234c0a86d4e97a621a93482b40ad8,

title = "Isothiourea-catalyzed formal enantioselective conjugate addition of benzophenone imines to {\ss}-fluorinated a,{\ss}-unsaturated esters",

abstract = "The isothiourea-catalyzed formal enantioselective conjugate addition of 2-hydroxybenzophenone imine derivatives to α,β-unsaturated para-nitrophenyl esters has been developed. Investigations of the scope and limitations of this procedure showed that β-electron withdrawing substituents within the α,β-unsaturated ester component was necessary for good product yield, giving rise to a range of β-imino ester and amide derivatives in moderate to good isolated yields with excellent enantioselectivity (20 examples, up to 81% yield and 97:3 er).",

author = "Jerson Lapetaje and Young, {Claire M.} and Chang Shu and Smith, {Andrew D.}",

note = "The DOST-SEI and DOST-Foreign Graduate Scholarship Program of the Philippines are thanked for a PhD scholarship (J. E. L) and the Royal Society for a Newton Fellowship (C. S.).",

year = "2022",

month = jun,

day = "21",

doi = "10.1039/D2CC01936A",

language = "English",

volume = "58",

pages = "6886--6889",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "49",

}

TY - JOUR

T1 - Isothiourea-catalyzed formal enantioselective conjugate addition of benzophenone imines to ß-fluorinated a,ß-unsaturated esters

AU - Lapetaje, Jerson

AU - Young, Claire M.

AU - Shu, Chang

AU - Smith, Andrew D.

N1 - The DOST-SEI and DOST-Foreign Graduate Scholarship Program of the Philippines are thanked for a PhD scholarship (J. E. L) and the Royal Society for a Newton Fellowship (C. S.).

PY - 2022/6/21

Y1 - 2022/6/21

N2 - The isothiourea-catalyzed formal enantioselective conjugate addition of 2-hydroxybenzophenone imine derivatives to α,β-unsaturated para-nitrophenyl esters has been developed. Investigations of the scope and limitations of this procedure showed that β-electron withdrawing substituents within the α,β-unsaturated ester component was necessary for good product yield, giving rise to a range of β-imino ester and amide derivatives in moderate to good isolated yields with excellent enantioselectivity (20 examples, up to 81% yield and 97:3 er).

AB - The isothiourea-catalyzed formal enantioselective conjugate addition of 2-hydroxybenzophenone imine derivatives to α,β-unsaturated para-nitrophenyl esters has been developed. Investigations of the scope and limitations of this procedure showed that β-electron withdrawing substituents within the α,β-unsaturated ester component was necessary for good product yield, giving rise to a range of β-imino ester and amide derivatives in moderate to good isolated yields with excellent enantioselectivity (20 examples, up to 81% yield and 97:3 er).

U2 - 10.1039/D2CC01936A

DO - 10.1039/D2CC01936A

M3 - Article

SN - 1359-7345

VL - 58

SP - 6886

EP - 6889

JO - Chemical Communications

JF - Chemical Communications

IS - 49

ER -

Isothiourea-catalyzed formal enantioselective conjugate addition of benzophenone imines to ß-fluorinated a,ß-unsaturated esters

Abstract

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Projects

Newton Fellowship Prof A Smith: Catalytic Enantioselective Synthesis of N-heterocycles using Lewis Base Catalysis

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data underpinning "Isothiourea-Catalyzed Enantioselective Conjugate Addition of Benzophenone Imine Derivatives to α,β-Unsaturated Esters"

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