X=Y-ZH systems as potential 1,3-dipoles. Part 21 activation of the ZH proton in imines.

Ronald Grigg; Gregory Donegan; H. Q.Nimal Gunaratne; Deirdre A. Kennedy; John F. Malone; Visuvanathar Sridharan; Sunit Thianpatanagul

doi:10.1016/S0040-4020(01)80037-5

X=Y-ZH systems as potential 1,3-dipoles. Part 21 activation of the ZH proton in imines.

Ronald Grigg^*, Gregory Donegan, H. Q.Nimal Gunaratne, Deirdre A. Kennedy, John F. Malone, Visuvanathar Sridharan, Sunit Thianpatanagul

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

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

72 Citations (Scopus)

Abstract

Imines, RCH=N-ZH, possessing a range of ZH groups (Z=CHCOPh, CHCOSR, CHCONHR, CHP(O)(OEt)₂, 2-CH-pyridyl, 2-CH-thiazolyl, and 9-fluorenyl) undergo thermal 1,2-prototropy generating azomethine ylides stereospecifically. The intermediate azomethine ylides undergo cycloaddition reactions with dipolarophiles either via an endo-transition state or via both endo- and exo-transition states to give polyfunctional pyrrolidines in good yield. In certain instances involving imines in which the amide activating group is present, the imine catalyses cis ⇌ trans isomerisation of the dipolarophile. X-Ray crystal structures of two of the cycloadducts are reported.

Original language	English
Pages (from-to)	1723-1746
Number of pages	24
Journal	Tetrahedron
Volume	45
Issue number	6
DOIs	https://doi.org/10.1016/S0040-4020(01)80037-5
Publication status	Published - 1989

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ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "X=Y-ZH systems as potential 1,3-dipoles. Part 21 activation of the ZH proton in imines.",

abstract = "Imines, RCH=N-ZH, possessing a range of ZH groups (Z=CHCOPh, CHCOSR, CHCONHR, CHP(O)(OEt)2, 2-CH-pyridyl, 2-CH-thiazolyl, and 9-fluorenyl) undergo thermal 1,2-prototropy generating azomethine ylides stereospecifically. The intermediate azomethine ylides undergo cycloaddition reactions with dipolarophiles either via an endo-transition state or via both endo- and exo-transition states to give polyfunctional pyrrolidines in good yield. In certain instances involving imines in which the amide activating group is present, the imine catalyses cis ⇌ trans isomerisation of the dipolarophile. X-Ray crystal structures of two of the cycloadducts are reported.",

author = "Ronald Grigg and Gregory Donegan and Gunaratne, {H. Q.Nimal} and Kennedy, {Deirdre A.} and Malone, {John F.} and Visuvanathar Sridharan and Sunit Thianpatanagul",

year = "1989",

doi = "10.1016/S0040-4020(01)80037-5",

language = "English",

volume = "45",

pages = "1723--1746",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

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T1 - X=Y-ZH systems as potential 1,3-dipoles. Part 21 activation of the ZH proton in imines.

AU - Grigg, Ronald

AU - Donegan, Gregory

AU - Gunaratne, H. Q.Nimal

AU - Kennedy, Deirdre A.

AU - Malone, John F.

AU - Sridharan, Visuvanathar

AU - Thianpatanagul, Sunit

PY - 1989

Y1 - 1989

N2 - Imines, RCH=N-ZH, possessing a range of ZH groups (Z=CHCOPh, CHCOSR, CHCONHR, CHP(O)(OEt)2, 2-CH-pyridyl, 2-CH-thiazolyl, and 9-fluorenyl) undergo thermal 1,2-prototropy generating azomethine ylides stereospecifically. The intermediate azomethine ylides undergo cycloaddition reactions with dipolarophiles either via an endo-transition state or via both endo- and exo-transition states to give polyfunctional pyrrolidines in good yield. In certain instances involving imines in which the amide activating group is present, the imine catalyses cis ⇌ trans isomerisation of the dipolarophile. X-Ray crystal structures of two of the cycloadducts are reported.

AB - Imines, RCH=N-ZH, possessing a range of ZH groups (Z=CHCOPh, CHCOSR, CHCONHR, CHP(O)(OEt)2, 2-CH-pyridyl, 2-CH-thiazolyl, and 9-fluorenyl) undergo thermal 1,2-prototropy generating azomethine ylides stereospecifically. The intermediate azomethine ylides undergo cycloaddition reactions with dipolarophiles either via an endo-transition state or via both endo- and exo-transition states to give polyfunctional pyrrolidines in good yield. In certain instances involving imines in which the amide activating group is present, the imine catalyses cis ⇌ trans isomerisation of the dipolarophile. X-Ray crystal structures of two of the cycloadducts are reported.

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U2 - 10.1016/S0040-4020(01)80037-5

DO - 10.1016/S0040-4020(01)80037-5

M3 - Article

AN - SCOPUS:45249128086

SN - 0040-4020

VL - 45

SP - 1723

EP - 1746

JO - Tetrahedron

JF - Tetrahedron

IS - 6

ER -

X=Y-ZH systems as potential 1,3-dipoles. Part 21 activation of the ZH proton in imines.

Abstract

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