Methyltrichlorosilane-DMSO: A facile and highly efficient recipe for the chlorination of enamides and enecarbamates

Synlett

Volumn , Issue 18, 2009, Pages 2961-2964

  Lin, Deqing ^a   Cheng, Ke ^a,b,c   Lu, Xiaoxia ^a   Sun, Jian ^a  

^a CHENGDU INSTITUTE OF BIOLOGY   (China)

^b CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Chlorination; Enamides; Enecarbamates; MeSiCl3 DMSO; Stereoselectivity

Indexed keywords

BETA CHLORO ENAMIDE; CARBAMIC ACID DERIVATIVE; DIMETHYL SULFOXIDE; ENAMIDE; ENAMINE; ENECARBAMATE; METHYLTRICHLOROSILANE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHLORINATION; ENZYME SPECIFICITY; ISOMERIZATION; ONE POT SYNTHESIS; STEREOCHEMISTRY;

EID: 72049107188     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218005     Document Type: Article

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28. General Procedure for the Chlorination of Enamides and Enecarbamtes To a solution of enamide or enecarbamte (0.1 mmol) in CH2Cl2 (1 mL) was added DMSO (0.15 mmol) and chlorosilane (0.2 mmol). After stirring at r.t. for 1 h, the reaction solution was quenched by sat. aq NaHCO3 (1 mL). The resulting mixture was extracted with EtOAc (3-5 mL). The combined organic layer was washed with brine (3-5 mL), dried over MgSO4, and concentrated under reduced pressure. The residue was purified through column chromatography on silica gel to give the desired bchlorinated enamide or enecarbamate.
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