Organocatalytic tandem three-component reaction of imine, alkyl vinyl ketone, and imide via aza-baylis-hillman reaction

Siang En Syu; Yu Ting Lee; Yeong Jiunn Jang; Wen-Wei Lin

doi:10.1021/jo102143r

Organocatalytic tandem three-component reaction of imine, alkyl vinyl ketone, and imide via aza-baylis-hillman reaction

Siang En Syu, Yu Ting Lee, Yeong Jiunn Jang, Wen-Wei Lin

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

Abstract

A highly chemoselective PPh₃-catalyzed three-component reaction of an imine, alkyl vinyl ketone, and phthalimide or succinimide is developed. Various highly functional adducts with high diastereoselectivities can be generated via aza-Morita-Baylis-Hillman reactions of aryl-substituted imines and alkyl vinyl ketones followed by Michael additions of imides and then epimerization.

Original language	English
Pages (from-to)	2888-2891
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	76
Issue number	8
DOIs	https://doi.org/10.1021/jo102143r
Publication status	Published - 2011 Apr 15

ASJC Scopus subject areas

Organic Chemistry

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abstract = "A highly chemoselective PPh3-catalyzed three-component reaction of an imine, alkyl vinyl ketone, and phthalimide or succinimide is developed. Various highly functional adducts with high diastereoselectivities can be generated via aza-Morita-Baylis-Hillman reactions of aryl-substituted imines and alkyl vinyl ketones followed by Michael additions of imides and then epimerization.",

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AU - Lee, Yu Ting

AU - Jang, Yeong Jiunn

AU - Lin, Wen-Wei

PY - 2011/4/15

Y1 - 2011/4/15

N2 - A highly chemoselective PPh3-catalyzed three-component reaction of an imine, alkyl vinyl ketone, and phthalimide or succinimide is developed. Various highly functional adducts with high diastereoselectivities can be generated via aza-Morita-Baylis-Hillman reactions of aryl-substituted imines and alkyl vinyl ketones followed by Michael additions of imides and then epimerization.

AB - A highly chemoselective PPh3-catalyzed three-component reaction of an imine, alkyl vinyl ketone, and phthalimide or succinimide is developed. Various highly functional adducts with high diastereoselectivities can be generated via aza-Morita-Baylis-Hillman reactions of aryl-substituted imines and alkyl vinyl ketones followed by Michael additions of imides and then epimerization.

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Organocatalytic tandem three-component reaction of imine, alkyl vinyl ketone, and imide via aza-baylis-hillman reaction

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