Modular One‐Step Three‐Component Synthesis of Tetrahydroisoquinolines Using a Catellani Strategy

Reported is a modular one‐step three‐component synthesis of tetrahydroisoquinolines using a Catellani strategy. This process exploits aziridines as the alkylating reagents, through palladium/norbornene cooperative catalysis, to enable a Catellani/Heck/aza‐Michael addition cascade. This mild, chemose...

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Published inAngewandte Chemie International Edition Vol. 57; no. 34; pp. 10980 - 10984
Main Authors Qian, Guangyin, Bai, Miao, Gao, Shijun, Chen, Han, Zhou, Siwei, Cheng, Hong‐Gang, Yan, Wei, Zhou, Qianghui
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 20.08.2018
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Alkylation
Aromatic compounds
Atom economy
aziridines
Catalysis
Catellani reaction
Chemistry
Chemistry, Multidisciplinary
cooperative catalysis
heterocycles
Palladium
Physical Sciences
Reagents
Regioselectivity
Science & Technology
Stereoselectivity
Substitutes
Substrates
Synthesis
aziridines
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
Catellani reaction
cooperative catalysis
ARYLATION
SEQUENTIAL ARYL-ARYL
N-H
STEREOSPECIFIC SYNTHESIS
FUNCTIONALIZATION
heterocycles
PALLADIUM-CATALYZED SYNTHESIS
CHEMISTRY
palladium
AZA-MICHAEL
Online AccessGet full text

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Abstract Reported is a modular one‐step three‐component synthesis of tetrahydroisoquinolines using a Catellani strategy. This process exploits aziridines as the alkylating reagents, through palladium/norbornene cooperative catalysis, to enable a Catellani/Heck/aza‐Michael addition cascade. This mild, chemoselective, and scalable protocol has broad substrate scope (43 examples, up to 90 % yield). The most striking feature of this protocol is the excellent regioselectivity and diastereoselectivity observed for 2‐alkyl‐ and 2‐aryl‐substituted aziridines to access 1,3‐cis‐substituted and 1,4‐cis‐substituted tetrahydroisoquinolines, respectively. Moreover, this is a versatile process with high step and atom economy. A modular synthesis of tetrahydroisoquinolines was developed. Aziridines act as the alkylating reagents to enable a Catellani/Heck/aza‐Michael addition cascade by palladium/norbornene (NBE) cooperative catalysis. This mild, chemoselective, and scalable protocol is compatible with a wide range of readily available aryl iodides, aziridines, and olefins. Excellent regio‐ and diastereoselectivities are observed for 1,3‐cis‐substituted and 1,4‐cis‐substituted tetrahydroisoquinolines.
AbstractList Reported is a modular one-step three-component synthesis of tetrahydroisoquinolines using a Catellani strategy. This process exploits aziridines as the alkylating reagents, through palladium/norbornene cooperative catalysis, to enable a Catellani/Heck/aza-Michael addition cascade. This mild, chemoselective, and scalable protocol has broad substrate scope (43 examples, up to 90% yield). The most striking feature of this protocol is the excellent regioselectivity and diastereoselectivity observed for 2-alkyl- and 2-aryl-substituted aziridines to access 1,3-cis-substituted and 1,4-cis-substituted tetrahydroisoquinolines, respectively. Moreover, this is a versatile process with high step and atom economy.
Reported is a modular one‐step three‐component synthesis of tetrahydroisoquinolines using a Catellani strategy. This process exploits aziridines as the alkylating reagents, through palladium/norbornene cooperative catalysis, to enable a Catellani/Heck/aza‐Michael addition cascade. This mild, chemoselective, and scalable protocol has broad substrate scope (43 examples, up to 90 % yield). The most striking feature of this protocol is the excellent regioselectivity and diastereoselectivity observed for 2‐alkyl‐ and 2‐aryl‐substituted aziridines to access 1,3‐cis‐substituted and 1,4‐cis‐substituted tetrahydroisoquinolines, respectively. Moreover, this is a versatile process with high step and atom economy. A modular synthesis of tetrahydroisoquinolines was developed. Aziridines act as the alkylating reagents to enable a Catellani/Heck/aza‐Michael addition cascade by palladium/norbornene (NBE) cooperative catalysis. This mild, chemoselective, and scalable protocol is compatible with a wide range of readily available aryl iodides, aziridines, and olefins. Excellent regio‐ and diastereoselectivities are observed for 1,3‐cis‐substituted and 1,4‐cis‐substituted tetrahydroisoquinolines.
Reported is a modular one‐step three‐component synthesis of tetrahydroisoquinolines using a Catellani strategy. This process exploits aziridines as the alkylating reagents, through palladium/norbornene cooperative catalysis, to enable a Catellani/Heck/aza‐Michael addition cascade. This mild, chemoselective, and scalable protocol has broad substrate scope (43 examples, up to 90 % yield). The most striking feature of this protocol is the excellent regioselectivity and diastereoselectivity observed for 2‐alkyl‐ and 2‐aryl‐substituted aziridines to access 1,3‐ cis ‐substituted and 1,4‐ cis ‐substituted tetrahydroisoquinolines, respectively. Moreover, this is a versatile process with high step and atom economy.
Reported is a modular one-step three-component synthesis of tetrahydroisoquinolines using a Catellani strategy. This process exploits aziridines as the alkylating reagents, through palladium/norbornene cooperative catalysis, to enable a Catellani/Heck/aza-Michael addition cascade. This mild, chemoselective, and scalable protocol has broad substrate scope (43 examples, up to 90 % yield). The most striking feature of this protocol is the excellent regioselectivity and diastereoselectivity observed for 2-alkyl- and 2-aryl-substituted aziridines to access 1,3-cis-substituted and 1,4-cis-substituted tetrahydroisoquinolines, respectively. Moreover, this is a versatile process with high step and atom economy.Reported is a modular one-step three-component synthesis of tetrahydroisoquinolines using a Catellani strategy. This process exploits aziridines as the alkylating reagents, through palladium/norbornene cooperative catalysis, to enable a Catellani/Heck/aza-Michael addition cascade. This mild, chemoselective, and scalable protocol has broad substrate scope (43 examples, up to 90 % yield). The most striking feature of this protocol is the excellent regioselectivity and diastereoselectivity observed for 2-alkyl- and 2-aryl-substituted aziridines to access 1,3-cis-substituted and 1,4-cis-substituted tetrahydroisoquinolines, respectively. Moreover, this is a versatile process with high step and atom economy.
Author Qian, Guangyin
Yan, Wei
Bai, Miao
Chen, Han
Gao, Shijun
Zhou, Qianghui
Zhou, Siwei
Cheng, Hong‐Gang
Author_xml – sequence: 1
  givenname: Guangyin
  surname: Qian
  fullname: Qian, Guangyin
  organization: Wuhan University
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  givenname: Miao
  surname: Bai
  fullname: Bai, Miao
  organization: Wuhan University
– sequence: 3
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  surname: Gao
  fullname: Gao, Shijun
  organization: Wuhan University
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  surname: Chen
  fullname: Chen, Han
  organization: Wuhan University
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  givenname: Siwei
  surname: Zhou
  fullname: Zhou, Siwei
  organization: Wuhan University
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  givenname: Hong‐Gang
  surname: Cheng
  fullname: Cheng, Hong‐Gang
  email: hgcheng@whu.edu.cn
  organization: Wuhan University
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  organization: Wuhan University
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  orcidid: 0000-0002-8125-0380
  surname: Zhou
  fullname: Zhou, Qianghui
  email: qhzhou@whu.edu.cn
  organization: Wuhan University
BackLink https://www.ncbi.nlm.nih.gov/pubmed/29956881$$D View this record in MEDLINE/PubMed
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Issue 34
Keywords aziridines
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
Catellani reaction
cooperative catalysis
ARYLATION
SEQUENTIAL ARYL-ARYL
N-H
STEREOSPECIFIC SYNTHESIS
FUNCTIONALIZATION
heterocycles
PALLADIUM-CATALYZED SYNTHESIS
CHEMISTRY
palladium
AZA-MICHAEL
Language English
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Notes Dedicated to Professor E. J. Corey on the occasion of his 90th birthday
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Snippet Reported is a modular one‐step three‐component synthesis of tetrahydroisoquinolines using a Catellani strategy. This process exploits aziridines as the...
Reported is a modular one-step three-component synthesis of tetrahydroisoquinolines using a Catellani strategy. This process exploits aziridines as the...
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SubjectTerms Alkylation
Aromatic compounds
Atom economy
aziridines
Catalysis
Catellani reaction
Chemistry
Chemistry, Multidisciplinary
cooperative catalysis
heterocycles
Palladium
Physical Sciences
Reagents
Regioselectivity
Science & Technology
Stereoselectivity
Substitutes
Substrates
Synthesis
Title Modular One‐Step Three‐Component Synthesis of Tetrahydroisoquinolines Using a Catellani Strategy
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.201806780
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000442863700032
https://www.ncbi.nlm.nih.gov/pubmed/29956881
https://www.proquest.com/docview/2087535705
https://www.proquest.com/docview/2062836760
Volume 57
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