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

Journal of Organic Chemistry

Volumn 76, Issue 8, 2011, Pages 2888-2891

  Syu, Siang En ^a   Lee, Yu Ting ^a   Jang, Yeong Jiunn ^a   Lin, Wenwei ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

BAYLIS-HILLMAN REACTIONS; CHEMOSELECTIVE; DIASTEREOSELECTIVITIES; EPIMERIZATION; MICHAEL ADDITIONS; MORITA-BAYLIS-HILLMAN REACTION; ORGANOCATALYTIC; PHTHALIMIDE; SUCCINIMIDE; THREE COMPONENT REACTIONS; VINYL KETONES;

ALKYLATION; KETONES; ORGANIC COMPOUNDS;

NITROGEN COMPOUNDS;

ALKYL VINYL KETONE; IMINE; KETONE DERIVATIVE; PHTHALIMIDE; SUCCINIMIDE; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; EPIMERIZATION; MICHAEL ADDITION; PROCESS OPTIMIZATION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 79953870516     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102143r     Document Type: Article

References (25)

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22. 1H NMR analysis when all the products were well dissolved in solution by adding excess of the corresponding solvent (Tables 1 - 3). The base, such as DABCO or an in situ formed base 10, accelerated the change of the ratio of two diastereomers of 5 or 6 in the solution.
23. For more details, please see the Supporting Information.
24. 3 was used as the representive catalyst for the reaction of 1, 2, and 3 in the proposed reaction mechanism, and even DABCO can also catalyze this process.
25. 3 were carried out. It was found that DABCO smoothly deprotonated the α-position of the ketone function of both erythro-5f and threo-5f. For mechanism studies, please see the Supporting Information.