A short and stereoselective synthesis of highly substituted cyclopropanes from α,β-unsaturated carbonyl compounds with dichloromethyl p-tolyl sulfoxide

Tetrahedron

Volumn 64, Issue 22, 2008, Pages 5279-5284

  Miyagawa, Toshifumi ^a   Tatenuma, Toshinori ^a   Tadokoro, Makoto ^a   Satoh, Tsuyoshi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Sulfinyl carbanion; Conjugate addition; Cyclopropane; Dichloromethyl p tolyl sulfoxide; Highly substituted cyclopropane

Indexed keywords

1 (2 CHLORO 1 METHYLCYCLOPROPYL) 4 PHENYLBUTAN 1 ONE; 1 [2 CHLORO 1 ETHYL 3 PHENETHYL 2 (TOLUENE 4 SULFINYL) CYCLOPROPYL]BUTAN 1 ONE; 1 [2 CHLORO 1 METHYL 2 (TOLUENE 4 SULFINYL)CYCLOPROPYL] 4 PHENYLNUTAN 1 ONE; 1 [2 CHLORO 1 METHYL 3 PHENETHYL 2 (TOLUENE 4 SULFINYL) CYCLOPROPYL]PROPAN 1 ONE; 1 BUTYL 2 CHLORO 2 (TOLUENE 4 SULFINYL)CYCLOPROPANE CARBOXYLIC ACID ETHYL ESTER; 1 BUTYL 2 CHLORO 3 METHYL 2 (TOLUENE 4 SULFINYL) CYCLOPROPANECARBOXYLIC ACID BENZYL ESTER; 1 CHLORO 2 PHENETHYL 1 (TOLUENE 4 SULFINYL) SPIRO[2.5]OCTAN 4 ONE; 2 CHLORO 1 METHYL 2 (TOLUENE 4 SULFINYL)CYCLOPROPANE CARBOXYLIC ACID ETHYL ESTER; 2 CHLORO 1 METHYL 2 (TOLUENE 4 SULFINYL)CYCYLOPROPANE CARBOXYLIC ACID BENZYL ESTER; 2 CHLORO 1 METHYL 3 PHENETHYL 2 (TOLUENE 4 SULFINYL) CYCLOPROANECARBOXYLIC ACID ETHYL ESTER; 2 CHLORO 1 METHYLCYCLOPROPANECARBOXYLIC ACID BENZYL ESTER; 2 CHLORO 1,3 DIMETHYL 2 (TOLUENE 4 SULFINYL) CYCLOPROPANECARBOXYLIC ACID BENZYL ESTER; 2 CHLORO 1,3 DIMETHYL 2 (TOLUENE 4 SULFONYL) CYCLOPROPANECARBOXYLIC ACID BENZYL ESTER; 2 CHLORO 1,3 DIMETHYLCYCLOPROPANECARBOXYLIC ACID BENZYL ESTER; 2 CHLORO 3 ETHYL 1 METHYL 2 (TOLUENE 4 SULFINYL) CYCLOPROPANECARBOXYLIC ACID BENZYL ESTER; 2 CHLORO 3 ETHYL 1 METHYLCYCLOPROAPNE CARBOXYLIC ACID BENZYL ESTER; [2 CHLORO 1 METHYL 2 (TOLUENE 4 SULFINYL)CYCLOPROPYL] PHENYLMETHANONE; [2 CHLORO 1 PROPYL 2 (TOLUENE 4 SULFINYL)CYCLOPROPYL] PHENYLMETHANONE; [2 CHLORO 3 ISOPROPYL 1 METHYL 2 (TOLUENE 4 SULFINYL) CYCLOPROPYL]PHENYLMETHANONE; CARBONYL DERIVATIVE; CYCLOPROPANE DERIVATIVE; SULFOXIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 42749094161     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.03.034     Document Type: Article

References (18)

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18. 3. The single crystals of 7c and 13f were mounted on glass fibers. Diffraction data were measured on a Bruker APEX CCD-Detector X-ray diffractometer with monochromated Mo Kα radiation from a rotating anode source apparatus. The data reduction, structure solution, and refinement, and all the necessary computational data processes were performed using APEX, SAINT, SHELXTL programs. Crystallographic data excluding structures have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 673248 for 7c and CCDC 673249 for 13f, respectively. A copy of the data can be obtained free of charge from CCDC, 12 Union road, Cambridge CB2 1EZ, UK [direct line: +44 1223 762910, fax: +44 (0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk.