Use of α-chlorosulfides in indium promoted C-C couplings: Easy entry into the stereoselective formation of epoxy alkynes

Tetrahedron Letters

Volumn 40, Issue 33, 1999, Pages 5967-5970

  Engstrom, Gregory ^a,b   Morelli, Meisha ^a,c   Palomo, Carolyn ^a   Mitzel, Thomas ^a  

^a TRINITY COLLEGE   (United States)

^b UNIVERSITY OF ARKANSAS   (United States)

^c AMHERST COLLEGE   (United States)

Author keywords

Indium couplings; Epoxy alkynes; Stereocontrol

Indexed keywords

ALKYNE; ALPHA CHLOROSULFIDE; INDIUM; SULFIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033551677     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01152-1     Document Type: Article

References (20)

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14. Diastereomeric products resulting from coupling of hexenal with the α-chlorosulfide were not separable by column chromatography, however, diastereomeric products resulting from coupling of benzaldehyde with the α-chlorosulfide were separable by column chromatography (hexanes:ethyl acetate 100:1) to give pure compounds.
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19. Example of reaction conditions for epoxy alkyne formation (benzaldehyde coupling product): To a stirring mixture of 80 mg (0.314 mmol) of the β-hydroxy thio ether in 5 mL of dichloromethane was added 52 mg (0.35 mmol) of trimethyloxoniumtetrafluoroborate. The solution was stirred at room temperature for 8 hours at which time thin layer chromatography revealed the absence of staring material. A solution of 7% sodium hydroxide (5 mL) was added with stirring for 15 minutes, the layers separated, and the organic layer dried over magnesium sulfate. The solvent was removed at room temperature and the crude material was purified via flash column chromatography (silica gel, 100:1 hexanes:ethyl acetate) to give a colorless oil. Yields were in the 65-80% range.
20. Previous use of trimethyloxoniumtetrafluoroborate: Pirkle, W. H.; Rinaldi, P. L. J. Org. Chem. 1978, 43, 3803.