Chemo‐ and Diastereoselective Construction of Indenopyrazolines via a Cascade aza‐Michael/Aldol Annulation of Huisgen Zwitterions with 2‐Arylideneindane‐1,3‐diones

A cascade aza‐Michael/Aldol annulation of 2‐arylideneindane‐1,3‐diones with in situ generated Huisgen zwitterions has been developed. This reaction afforded the desired products in moderate to good yields (up to 87%) with excellent chemo‐ and diastereoselectivity (up to 20:1). This strategy allows f...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 359; no. 23; pp. 4158 - 4164
Main Authors Li, Yuming, Zhang, Haikun, Wei, Rong, Miao, Zhiwei
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 11.12.2017
Wiley Subscription Services, Inc
Subjects
Aldehydes
aza-Michael/Aldol annulation
Chemical reactions
Chemistry
Chemistry, Applied
Chemistry, Organic
Chemoselectivity
Diastereoselectivity
Huisgen zwitterions
Indenopyrazolines
Organic chemistry
Physical Sciences
Science & Technology
Zwitterions
PHOSPHINE
ENANTIOSELECTIVE SYNTHESIS
Chemoselectivity
DIETHYL AZODICARBOXYLATE
aza-Michael/Aldol annulation
Huisgen zwitterions
Diastereoselectivity
MITSUNOBU REACTION
CYCLOADDITION
DIALKYL AZODICARBOXYLATE
Indenopyrazolines
SYNTHETIC STRATEGY
TRIPHENYLPHOSPHINE-MEDIATED REACTION
PYRAZOLINES
DERIVATIVES
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Summary:A cascade aza‐Michael/Aldol annulation of 2‐arylideneindane‐1,3‐diones with in situ generated Huisgen zwitterions has been developed. This reaction afforded the desired products in moderate to good yields (up to 87%) with excellent chemo‐ and diastereoselectivity (up to 20:1). This strategy allows facile diastereoselective preparation of biologically important indenopyrazoline derivatives containing two contiguous chiral centers including a quaternary stereogenic center.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201701013