Enantioselective protonation of itaconimides with thiols and the rotational kinetics of the axially chiral C-N bond

Shishi Lin; Dasheng Leow; Kuo Wei Huang; Choon Hong Tan

doi:10.1002/asia.200900331

Enantioselective protonation of itaconimides with thiols and the rotational kinetics of the axially chiral C-N bond

Shishi Lin^*, Dasheng Leow, Kuo Wei Huang, Choon Hong Tan

^*Corresponding author for this work

Physical Sciences and Engineering

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

57 Scopus citations

Abstract

Bicyclic guanidines are able to catalyze the protonation reactions of 2- phthalimidoacrylates with thiols in excellent yields and enantioselectivities. The protonation reaction of itaconimides with secondary phosphine oxides is also known. Herein, the tandem conjugate addition-enantioselective protonation of Nsubstituted itaconimides with thiols catalyzed by chiral bicyclic guanidine is investigated. The rotational barrier of the C-N axis of N-2-tert-butyl phenylitaconimide is also studied, both experimentally and computationally.

Original language	English (US)
Pages (from-to)	1741-1744
Number of pages	4
Journal	Chemistry - An Asian Journal
Volume	4
Issue number	11
DOIs	https://doi.org/10.1002/asia.200900331
State	Published - Nov 2 2009

Keywords

Asymmetric catalysis
Atropisomerism
Guanidines
Organocatalysis
Protonation

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

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10.1002/asia.200900331

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title = "Enantioselective protonation of itaconimides with thiols and the rotational kinetics of the axially chiral C-N bond",

abstract = "Bicyclic guanidines are able to catalyze the protonation reactions of 2- phthalimidoacrylates with thiols in excellent yields and enantioselectivities. The protonation reaction of itaconimides with secondary phosphine oxides is also known. Herein, the tandem conjugate addition-enantioselective protonation of Nsubstituted itaconimides with thiols catalyzed by chiral bicyclic guanidine is investigated. The rotational barrier of the C-N axis of N-2-tert-butyl phenylitaconimide is also studied, both experimentally and computationally.",

keywords = "Asymmetric catalysis, Atropisomerism, Guanidines, Organocatalysis, Protonation",

author = "Shishi Lin and Dasheng Leow and Huang, {Kuo Wei} and Tan, {Choon Hong}",

year = "2009",

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T1 - Enantioselective protonation of itaconimides with thiols and the rotational kinetics of the axially chiral C-N bond

AU - Lin, Shishi

AU - Leow, Dasheng

AU - Huang, Kuo Wei

AU - Tan, Choon Hong

PY - 2009/11/2

Y1 - 2009/11/2

N2 - Bicyclic guanidines are able to catalyze the protonation reactions of 2- phthalimidoacrylates with thiols in excellent yields and enantioselectivities. The protonation reaction of itaconimides with secondary phosphine oxides is also known. Herein, the tandem conjugate addition-enantioselective protonation of Nsubstituted itaconimides with thiols catalyzed by chiral bicyclic guanidine is investigated. The rotational barrier of the C-N axis of N-2-tert-butyl phenylitaconimide is also studied, both experimentally and computationally.

AB - Bicyclic guanidines are able to catalyze the protonation reactions of 2- phthalimidoacrylates with thiols in excellent yields and enantioselectivities. The protonation reaction of itaconimides with secondary phosphine oxides is also known. Herein, the tandem conjugate addition-enantioselective protonation of Nsubstituted itaconimides with thiols catalyzed by chiral bicyclic guanidine is investigated. The rotational barrier of the C-N axis of N-2-tert-butyl phenylitaconimide is also studied, both experimentally and computationally.

KW - Asymmetric catalysis

KW - Atropisomerism

KW - Guanidines

KW - Organocatalysis

KW - Protonation

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DO - 10.1002/asia.200900331

M3 - Article

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AN - SCOPUS:73649120620

SN - 1861-4728

VL - 4

SP - 1741

EP - 1744

JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

IS - 11

ER -

Enantioselective protonation of itaconimides with thiols and the rotational kinetics of the axially chiral C-N bond

Abstract

Keywords

ASJC Scopus subject areas

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