Organocatalyzed [2+2] Cycloaddition Reactions between Quinone Imine Ketals and Allenoates

A new cycloaddition reaction of quinone imine ketals (QIKs), which could be utilized to the construction of functionalized azaspirocyclics under mild conditions, is described. This transformation involved a [2+2] cycloaddition reaction between QIKs and allenoates catalyzed by DABCO, and then treatme...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 53; no. 3; pp. 518 - 526
Main Authors Liu, Teng, He, Chixian, Wang, Fan, Shen, Xiang, Li, Yongqin, Lang, Man, Li, Guijun, Huang, Chao, Cheng, Feixiang
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 03.02.2021
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
allenoates
MORITA-BAYLIS-HILLMAN
ACTIVATION
CARBON
ASYMMETRIC DIELS-ALDER
[2+2] cycloaddition
E-selectivity
IPSO-CYCLIZATION
INDOLES
CASCADE REACTION
quinone imine ketals
CHEMO
MONOACETALS
ACCESS
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Summary:A new cycloaddition reaction of quinone imine ketals (QIKs), which could be utilized to the construction of functionalized azaspirocyclics under mild conditions, is described. This transformation involved a [2+2] cycloaddition reaction between QIKs and allenoates catalyzed by DABCO, and then treatment with 1 N HCl in one-pot. The strategy could provide a practical route to access azetidine-fused spirohexadienones in good to excellent yields and with high E-selectivity.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0040-1707292