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Cross-conjugated Trienamine Catalysis with alpha '-Alkylidene 2-Cyclohexenones: Application in beta , gamma -Regioselective Aza-Diels-Alder Reaction

Endo-type cross-conjugated trienamines between highly congested alpha '-alkylidene 2-cyclohexenones and a chiral primary amine catalyst serve as HOMO-raised dienophiles in inverse-electron-demand aza-Diels-Alder cycloadditions with a number of 1-azadiene substrates. The reactions exhibit exclusive b... Full description

Journal Title: Chemistry: A European Journal February 2017, Vol.23(12), pp.2945-2949
Main Author: Zhou, Zhi
Other Authors: Wang, Zhou-Xiang , Ouyang, Qin , Xiao, Wei , Du, Wei , Chen, Ying-Chun
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201605606
Link: http://search.proquest.com/docview/1884116982/?pq-origsite=primo
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title: Cross-conjugated Trienamine Catalysis with alpha '-Alkylidene 2-Cyclohexenones: Application in beta , gamma -Regioselective Aza-Diels-Alder Reaction
format: Article
creator:
  • Zhou, Zhi
  • Wang, Zhou-Xiang
  • Ouyang, Qin
  • Xiao, Wei
  • Du, Wei
  • Chen, Ying-Chun
subjects:
  • Cycloaddition
  • Complexity
  • Substrates
  • Catalysts
  • Amines
  • Stereoselectivity
  • Catalysis
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
ispartof: Chemistry: A European Journal, February 2017, Vol.23(12), pp.2945-2949
description: Endo-type cross-conjugated trienamines between highly congested alpha '-alkylidene 2-cyclohexenones and a chiral primary amine catalyst serve as HOMO-raised dienophiles in inverse-electron-demand aza-Diels-Alder cycloadditions with a number of 1-azadiene substrates. The reactions exhibit exclusive beta , gamma -regioselectivity, and multifunctional products with high molecular complexity are efficiently constructed in excellent diastereo- and enantioselectivity (>19:1 d.r., up to 99%ee). Raising the bar: Endo-type cross- conjugated trienamines between alpha '-alkylidene 2-cyclohexenones and a chiral primary amine catalyst serve as HOMO-raised dienophiles in inverse-electron-demand aza-Diels-Alder cycloadditions with a number of 1-azadiene substrates. A diversity of chiral heterocyclic systems was thus efficiently constructed in excellent stereoselectivity.
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201605606
fulltext: fulltext
issn:
  • 09476539
  • 0947-6539
  • 15213765
  • 1521-3765
url: Link


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titleCross-conjugated Trienamine Catalysis with alpha '-Alkylidene 2-Cyclohexenones: Application in beta , gamma -Regioselective Aza-Diels-Alder Reaction
creatorZhou, Zhi ; Wang, Zhou-Xiang ; Ouyang, Qin ; Xiao, Wei ; Du, Wei ; Chen, Ying-Chun
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subjectCycloaddition ; Complexity ; Substrates ; Catalysts ; Amines ; Stereoselectivity ; Catalysis ; Analysis (MD) ; Chemical Analysis (Ep) ; Chemical Analysis (Ed) ; Chemical Analysis (EC)
descriptionEndo-type cross-conjugated trienamines between highly congested alpha '-alkylidene 2-cyclohexenones and a chiral primary amine catalyst serve as HOMO-raised dienophiles in inverse-electron-demand aza-Diels-Alder cycloadditions with a number of 1-azadiene substrates. The reactions exhibit exclusive beta , gamma -regioselectivity, and multifunctional products with high molecular complexity are efficiently constructed in excellent diastereo- and enantioselectivity (>19:1 d.r., up to 99%ee). Raising the bar: Endo-type cross- conjugated trienamines between alpha '-alkylidene 2-cyclohexenones and a chiral primary amine catalyst serve as HOMO-raised dienophiles in inverse-electron-demand aza-Diels-Alder cycloadditions with a number of 1-azadiene substrates. A diversity of chiral heterocyclic systems was thus efficiently constructed in excellent stereoselectivity.
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titleCross-conjugated Trienamine Catalysis with alpha '-Alkylidene 2-Cyclohexenones: Application in beta , gamma -Regioselective Aza-Diels-Alder Reaction
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abstractEndo-type cross-conjugated trienamines between highly congested alpha '-alkylidene 2-cyclohexenones and a chiral primary amine catalyst serve as HOMO-raised dienophiles in inverse-electron-demand aza-Diels-Alder cycloadditions with a number of 1-azadiene substrates. The reactions exhibit exclusive beta , gamma -regioselectivity, and multifunctional products with high molecular complexity are efficiently constructed in excellent diastereo- and enantioselectivity (>19:1 d.r., up to 99%ee). Raising the bar: Endo-type cross- conjugated trienamines between alpha '-alkylidene 2-cyclohexenones and a chiral primary amine catalyst serve as HOMO-raised dienophiles in inverse-electron-demand aza-Diels-Alder cycloadditions with a number of 1-azadiene substrates. A diversity of chiral heterocyclic systems was thus efficiently constructed in excellent stereoselectivity.
doi10.1002/chem.201605606
urlhttp://search.proquest.com/docview/1884116982/
orcididhttp://orcid.org/0000-0003-1902-0979
date2017-02-24