Chemo-, Diastereo-, and Enantioselective Iridium-Catalyzed Allylic Intramolecular Dearomatization Reaction of Naphthol Derivatives

An iridium‐catalyzed intramolecular asymmetric allylic dearomatization reaction of naphthol derivatives is described. Challenges confronted in this reaction include chemoselectivity between carbon and oxygen atoms as nucleophilic centers, diastereoselectivity when contiguous chiral centers are gener...

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Published inAngewandte Chemie International Edition Vol. 55; no. 10; pp. 3496 - 3499
Main Authors Cheng, Qiang, Wang, Ye, You, Shu-Li
Format Journal Article
LanguageEnglish
Published WEINHEIM Blackwell Publishing Ltd 01.03.2016
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
aromaticity
asymmetric catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Derivatives
Enantiomers
Iridium
ligand effects
Naphthol
Nuclei
Oxygen atoms
Physical Sciences
Science & Technology
Selectivity
spiro compounds
ASYMMETRIC DEAROMATIZATION
SUBSTITUTION
ARYLATIVE DEAROMATIZATION
ALKYLATION
ALLYLATION
PHOSPHORAMIDITE
asymmetric catalysis
spiro compounds
INDOLES
iridium
PHENOLS
CONSTRUCTION
STEREOGENIC CENTERS
aromaticity
ligand effects
Online AccessGet full text
ISSN1433-7851
1521-3773
1521-3773
DOI10.1002/anie.201511519

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Abstract An iridium‐catalyzed intramolecular asymmetric allylic dearomatization reaction of naphthol derivatives is described. Challenges confronted in this reaction include chemoselectivity between carbon and oxygen atoms as nucleophilic centers, diastereoselectivity when contiguous chiral centers are generated, and enantioselective control for constructing an all‐carbon quaternary stereocenter. In the presence of an iridium catalyst generated from [{Ir(dbcot)Cl}2] (dbcot=dibenzocyclooctatetraene) and a new THQphos (tetrahydroquinolinedinaphthophosphoramidite) ligand, various spironaphthalenones were obtained with up to greater than 95:5 C/O selectivity, greater than 95:5 d.r., and 99 % ee, thus providing a general method for the dearomatization of naphthols. Triple challenge: The challenges addressed in the title reaction include chemoselectivity between C and O as nucleophiles, diastereoselectivity when contiguous chiral centers are generated, and enantioselective control for constructing an all‐carbon quaternary stereocenter. The [{Ir(dbcot)Cl}2]/(S,Sa)‐L system leads to a general method for the dearomatization of naphthols. dbcot=dibenzocyclooctatetraene.
AbstractList An iridium-catalyzed intramolecular asymmetric allylic dearomatization reaction of naphthol derivatives is described. Challenges confronted in this reaction include chemoselectivity between carbon and oxygen atoms as nucleophilic centers, diastereoselectivity when contiguous chiral centers are generated, and enantioselective control for constructing an all-carbon quaternary stereocenter. In the presence of an iridium catalyst generated from [{Ir(dbcot)Cl}2] (dbcot=dibenzocyclooctatetraene) and a new THQphos (tetrahydroquinolinedinaphthophosphoramidite) ligand, various spironaphthalenones were obtained with up to greater than 95:5 C/O selectivity, greater than 95:5 d.r., and 99 % ee, thus providing a general method for the dearomatization of naphthols.An iridium-catalyzed intramolecular asymmetric allylic dearomatization reaction of naphthol derivatives is described. Challenges confronted in this reaction include chemoselectivity between carbon and oxygen atoms as nucleophilic centers, diastereoselectivity when contiguous chiral centers are generated, and enantioselective control for constructing an all-carbon quaternary stereocenter. In the presence of an iridium catalyst generated from [{Ir(dbcot)Cl}2] (dbcot=dibenzocyclooctatetraene) and a new THQphos (tetrahydroquinolinedinaphthophosphoramidite) ligand, various spironaphthalenones were obtained with up to greater than 95:5 C/O selectivity, greater than 95:5 d.r., and 99 % ee, thus providing a general method for the dearomatization of naphthols.
An iridium-catalyzed intramolecular asymmetric allylic dearomatization reaction of naphthol derivatives is described. Challenges confronted in this reaction include chemoselectivity between carbon and oxygen atoms as nucleophilic centers, diastereoselectivity when contiguous chiral centers are generated, and enantioselective control for constructing an all-carbon quaternary stereocenter. In the presence of an iridium catalyst generated from [{Ir(dbcot)Cl}(2)] (dbcot=dibenzocyclooctatetraene) and a new THQphos (tetrahydroquinolinedinaphthophosphoramidite) ligand, various spironaphthalenones were obtained with up to greater than 95:5 C/O selectivity, greater than 95:5 d.r., and 99% ee, thus providing a general method for the dearomatization of naphthols.
An iridium‐catalyzed intramolecular asymmetric allylic dearomatization reaction of naphthol derivatives is described. Challenges confronted in this reaction include chemoselectivity between carbon and oxygen atoms as nucleophilic centers, diastereoselectivity when contiguous chiral centers are generated, and enantioselective control for constructing an all‐carbon quaternary stereocenter. In the presence of an iridium catalyst generated from [{Ir(dbcot)Cl} 2 ] (dbcot=dibenzocyclooctatetraene) and a new THQphos (tetrahydroquinolinedinaphthophosphoramidite) ligand, various spironaphthalenones were obtained with up to greater than 95:5 C/O selectivity, greater than 95:5 d.r., and 99 % ee , thus providing a general method for the dearomatization of naphthols.
An iridium‐catalyzed intramolecular asymmetric allylic dearomatization reaction of naphthol derivatives is described. Challenges confronted in this reaction include chemoselectivity between carbon and oxygen atoms as nucleophilic centers, diastereoselectivity when contiguous chiral centers are generated, and enantioselective control for constructing an all‐carbon quaternary stereocenter. In the presence of an iridium catalyst generated from [{Ir(dbcot)Cl}2] (dbcot=dibenzocyclooctatetraene) and a new THQphos (tetrahydroquinolinedinaphthophosphoramidite) ligand, various spironaphthalenones were obtained with up to greater than 95:5 C/O selectivity, greater than 95:5 d.r., and 99 % ee, thus providing a general method for the dearomatization of naphthols. Triple challenge: The challenges addressed in the title reaction include chemoselectivity between C and O as nucleophiles, diastereoselectivity when contiguous chiral centers are generated, and enantioselective control for constructing an all‐carbon quaternary stereocenter. The [{Ir(dbcot)Cl}2]/(S,Sa)‐L system leads to a general method for the dearomatization of naphthols. dbcot=dibenzocyclooctatetraene.
Author Cheng, Qiang
You, Shu-Li
Wang, Ye
Author_xml – sequence: 1
  givenname: Qiang
  surname: Cheng
  fullname: Cheng, Qiang
  organization: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, 200032, Shanghai, China
– sequence: 2
  givenname: Ye
  surname: Wang
  fullname: Wang, Ye
  organization: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, 200032, Shanghai, China
– sequence: 3
  givenname: Shu-Li
  surname: You
  fullname: You, Shu-Li
  email: slyou@sioc.ac.cn
  organization: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, 200032, Shanghai, China
BackLink https://www.ncbi.nlm.nih.gov/pubmed/26848021$$D View this record in MEDLINE/PubMed
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Issue 10
Keywords ASYMMETRIC DEAROMATIZATION
SUBSTITUTION
ARYLATIVE DEAROMATIZATION
ALKYLATION
ALLYLATION
PHOSPHORAMIDITE
asymmetric catalysis
spiro compounds
INDOLES
iridium
PHENOLS
CONSTRUCTION
STEREOGENIC CENTERS
aromaticity
ligand effects
Language English
License http://onlinelibrary.wiley.com/termsAndConditions#vor
2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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ArticleID:ANIE201511519
National Basic Research Program of China - No. 2015CB856600
National Natural Science Foundation of China - No. 21332009; No. 21421091
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2010; 12
2007; 107
2015; 6
2004 2004; 43 116
2004; 126
2011; 2
2013; 45
2004; 8
2004; 7
2009
2014; 47
2007
2012; 18
2007; 72
2011; 34
2012; 38
2013; 340
2008 2008; 47 120
2012; 14
2015; 7
2014; 136
2012; 10
2011; 133
2004; 10
2010; 43
2012; 134
2015; 137
2012 2012; 51 124
2015; 21
2010; 132
2015 2015; 54 127
2013; 135
2011 2011; 50 123
2000; 100
2000; 122
2014
2003; 125
2012; 23
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1998; 120
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Snippet An iridium‐catalyzed intramolecular asymmetric allylic dearomatization reaction of naphthol derivatives is described. Challenges confronted in this reaction...
An iridium-catalyzed intramolecular asymmetric allylic dearomatization reaction of naphthol derivatives is described. Challenges confronted in this reaction...
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SubjectTerms aromaticity
asymmetric catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Derivatives
Enantiomers
Iridium
ligand effects
Naphthol
Nuclei
Oxygen atoms
Physical Sciences
Science & Technology
Selectivity
spiro compounds
Title Chemo-, Diastereo-, and Enantioselective Iridium-Catalyzed Allylic Intramolecular Dearomatization Reaction of Naphthol Derivatives
URI https://api.istex.fr/ark:/67375/WNG-G6TMJQRX-4/fulltext.pdf
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https://www.ncbi.nlm.nih.gov/pubmed/26848021
https://www.proquest.com/docview/1768077438
https://www.proquest.com/docview/1906607960
https://www.proquest.com/docview/1768561074
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