Catalytic Asymmetric Cycloaddition of In Situ-Generated ortho-Quinone Methides and Azlactones by a Triple Brønsted Acid Activation Strategy

A convergent and highly stereoselective [4+2] cycloaddition of in situ‐generated ortho‐Quinone methides (o‐QMs) and azlactone enols has been successfully developed through a triple Brønsted acid catalysis strategy. This protocol provides an efficient and mild access to various densely functionalized...

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Published inChemistry : a European journal Vol. 22; no. 20; pp. 6774 - 6778
Main Authors Yu, Xiao-Ye, Chen, Jia-Rong, Wei, Qiang, Cheng, Hong-Gang, Liu, Zhi-Cheng, Xiao, Wen-Jing
Format Journal Article
LanguageEnglish
Published WEINHEIM Blackwell Publishing Ltd 10.05.2016
Wiley
Wiley Subscription Services, Inc
Subjects
Activation
Asymmetry
Bearing
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cycloaddition
Enantiomers
heterocycles
lactones
methides
Physical Sciences
Quinones
Science & Technology
Strategy
synthetic methods
SULFUR YLIDES
ENANTIOSELECTIVE SYNTHESIS
TRIARYLMETHANES
methides
FORMAL 4+1 ANNULATION
CLASSIFICATION
lactones
cycloaddition
heterocycles
DIELS-ALDER REACTION
CONSTRUCTION
DERIVATIVES
synthetic methods
IN-SITU
DIHYDROCOUMARINS
Online AccessGet full text

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Abstract A convergent and highly stereoselective [4+2] cycloaddition of in situ‐generated ortho‐Quinone methides (o‐QMs) and azlactone enols has been successfully developed through a triple Brønsted acid catalysis strategy. This protocol provides an efficient and mild access to various densely functionalized dihydrocoumarins bearing adjacent quaternary and tertiary stereogenic centers in high yields with excellent diastereo‐ and enantioselectivity. Triple activation! A convergent and highly stereoselective [4+2] cycloaddition of in situ generated ortho‐Quinone methides (o‐QMs) and azlactone enols has been successfully developed through a triple Brønsted acid catalysis strategy. This protocol provides an efficient and mild access to various densely functionalized dihydrocoumarins (see scheme).
AbstractList A convergent and highly stereoselective [4+2] cycloaddition of in situ‐generated ortho ‐Quinone methides ( o ‐QMs) and azlactone enols has been successfully developed through a triple Brønsted acid catalysis strategy. This protocol provides an efficient and mild access to various densely functionalized dihydrocoumarins bearing adjacent quaternary and tertiary stereogenic centers in high yields with excellent diastereo‐ and enantioselectivity.
A convergent and highly stereoselective [4+2] cycloaddition of in situ-generated ortho-Quinone methides (o-QMs) and azlactone enols has been successfully developed through a triple BrOnsted acid catalysis strategy. This protocol provides an efficient and mild access to various densely functionalized dihydrocoumarins bearing adjacent quaternary and tertiary stereogenic centers in high yields with excellent diastereo- and enantioselectivity.
A convergent and highly stereoselective [4+2] cycloaddition of in situ‐generated ortho‐Quinone methides (o‐QMs) and azlactone enols has been successfully developed through a triple Brønsted acid catalysis strategy. This protocol provides an efficient and mild access to various densely functionalized dihydrocoumarins bearing adjacent quaternary and tertiary stereogenic centers in high yields with excellent diastereo‐ and enantioselectivity. Triple activation! A convergent and highly stereoselective [4+2] cycloaddition of in situ generated ortho‐Quinone methides (o‐QMs) and azlactone enols has been successfully developed through a triple Brønsted acid catalysis strategy. This protocol provides an efficient and mild access to various densely functionalized dihydrocoumarins (see scheme).
A convergent and highly stereoselective [4+2] cycloaddition of in situ-generated ortho-Quinone methides (o-QMs) and azlactone enols has been successfully developed through a triple Brønsted acid catalysis strategy. This protocol provides an efficient and mild access to various densely functionalized dihydrocoumarins bearing adjacent quaternary and tertiary stereogenic centers in high yields with excellent diastereo- and enantioselectivity.
A convergent and highly stereoselective [4+2] cycloaddition of in situ-generated ortho-Quinone methides (o-QMs) and azlactone enols has been successfully developed through a triple Brønsted acid catalysis strategy. This protocol provides an efficient and mild access to various densely functionalized dihydrocoumarins bearing adjacent quaternary and tertiary stereogenic centers in high yields with excellent diastereo- and enantioselectivity.A convergent and highly stereoselective [4+2] cycloaddition of in situ-generated ortho-Quinone methides (o-QMs) and azlactone enols has been successfully developed through a triple Brønsted acid catalysis strategy. This protocol provides an efficient and mild access to various densely functionalized dihydrocoumarins bearing adjacent quaternary and tertiary stereogenic centers in high yields with excellent diastereo- and enantioselectivity.
Author Chen, Jia-Rong
Cheng, Hong-Gang
Yu, Xiao-Ye
Liu, Zhi-Cheng
Wei, Qiang
Xiao, Wen-Jing
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  surname: Wei
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  organization: CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, 430079, Hubei, P. R. China
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  fullname: Cheng, Hong-Gang
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  fullname: Liu, Zhi-Cheng
  organization: CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, 430079, Hubei, P. R. China
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  surname: Xiao
  fullname: Xiao, Wen-Jing
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2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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Issue 20
Keywords SULFUR YLIDES
ENANTIOSELECTIVE SYNTHESIS
TRIARYLMETHANES
methides
FORMAL 4+1 ANNULATION
CLASSIFICATION
lactones
cycloaddition
heterocycles
DIELS-ALDER REACTION
CONSTRUCTION
DERIVATIVES
synthetic methods
IN-SITU
DIHYDROCOUMARINS
Language English
License http://onlinelibrary.wiley.com/termsAndConditions#vor
2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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National Natural Science Foundation of China - No. 21272087; No. 21472058; No. 21232003; No. 21202053
Youth Chen-Guang Project of Wuhan - No. 2015070404010180
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PublicationDecade 2010
PublicationPlace WEINHEIM
PublicationPlace_xml – name: WEINHEIM
– name: Germany
– name: Weinheim
PublicationSubtitle A European Journal
PublicationTitle Chemistry : a European journal
PublicationTitleAbbrev CHEM-EUR J
PublicationTitleAlternate Chem. Eur. J
PublicationYear 2016
Publisher Blackwell Publishing Ltd
Wiley
Wiley Subscription Services, Inc
Publisher_xml – name: Blackwell Publishing Ltd
– name: Wiley
– name: Wiley Subscription Services, Inc
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2014 2014; 53 126
2015; 35
2002; 58
2007; 107
2011; 13
2009; 351
2011; 17
2014; 136
2007; 36
2013 2013; 52 125
2013; 19
2013; 18
2014; 4
2015; 137
2005; 102
2012 2012; 51 124
2015 2015; 54 127
2013; 355
2011; 67
2016; 358
2000; 287
2016; 81
2009; 15
2010; 8
2015; 13
2012; 80
2007; 129
2015; 17
2012
2011
2013; 46
2015; 51
2010
2004; 47
2002; 35
2011; 40
2009
1997
2007
2014; 47
2011; 76
2004
2009; 131
2011; 6
2014; 114
2011; 133
2014; 43
2010; 43
2012; 3
2016 2016; 55 128
2015; 115
2015; 357
2015; 20
2015; 21
2010; 132
2013; 135
2015
2014
2013
2012; 45
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Zamfir A. (e_1_2_2_90_2) 2010; 8
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(e_1_2_2_3_2) 2009
Wang Z.-B. (e_1_2_2_29_2) 2015
e_1_2_2_91_2
Moss R. A. (e_1_2_2_2_2) 2004
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Kennedy R. O (e_1_2_2_95_2) 1997
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Yang, Q.-Q. (000375866600011.82) 2012; 124
Koch, MA (WOS:000233762000004) 2005; 102
Izquierdo, J (WOS:000322432400014) 2013; 135
Chen, DF (WOS:000340702000014) 2014; 47
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Zhao, W. (000375866600011.89) 2015; 127
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Ding, K.-L. (000375866600011.20) 2012
Chen, JR (WOS:000356316300016) 2015; 115
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Rueping, M (WOS:000288889900013) 2011; 133
Hsiao, CC (WOS:000354193300047) 2015; 54
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Barker, A (WOS:000316427000011) 2013; 18
Moss, R. A. (000375866600011.55) 2004
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Fisk, JS (WOS:000248353600004) 2007; 36
Lv, H (WOS:000272392000012) 2009; 351
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Liao, H. H. (000375866600011.48) 2015; 127
Bai, WJ (WOS:000346683200025) 2014; 47
Sun, W. (000375866600011.69) 2013; 125
Hu, HP (WOS:000349990600029) 2015; 51
Jiang, XX (WOS:000314653800009) 2013; 355
Albini, A (WOS:000336996600010) 2013
Xuan, J. (000375866600011.79) 2015; 127
Lee, A (WOS:000339693900011) 2014; 136
Fisk, JS (WOS:000244896900014) 2007; 129
Chen, J.-R. (000375866600011.16) 2014; 126
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Hsiao, C.-C. (000375866600011.32) 2015; 127
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El-Sepelgy, O. (000375866600011.25) 2014; 126
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Zhang, Y (WOS:000244896900023) 2007; 129
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Snippet A convergent and highly stereoselective [4+2] cycloaddition of in situ‐generated ortho‐Quinone methides (o‐QMs) and azlactone enols has been successfully...
A convergent and highly stereoselective [4+2] cycloaddition of in situ‐generated ortho ‐Quinone methides ( o ‐QMs) and azlactone enols has been successfully...
A convergent and highly stereoselective [4+2] cycloaddition of in situ-generated ortho-Quinone methides (o-QMs) and azlactone enols has been successfully...
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SubjectTerms Activation
Asymmetry
Bearing
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cycloaddition
Enantiomers
heterocycles
lactones
methides
Physical Sciences
Quinones
Science & Technology
Strategy
synthetic methods
Title Catalytic Asymmetric Cycloaddition of In Situ-Generated ortho-Quinone Methides and Azlactones by a Triple Brønsted Acid Activation Strategy
URI https://api.istex.fr/ark:/67375/WNG-0MQ7CH89-9/fulltext.pdf
https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fchem.201601227
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https://www.ncbi.nlm.nih.gov/pubmed/26990670
https://www.proquest.com/docview/1786243147
https://www.proquest.com/docview/1907556533
https://www.proquest.com/docview/1787086218
Volume 22
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