Stereoselective synthesis of 2,3-epoxy alcohols mediated by a remote sulfinyl group

Tetrahedron

Volumn 66, Issue 8, 2010, Pages 1581-1585

  García Ruano, José Luis ^a   Martín Castro, Ana M ^a   Tato, Francisco ^a   Torrente, Esther ^a   Tocco, M Giovanna ^a,b   Florio, Saverio ^b   Capriati, Vito ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSITY OF BARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 BROMOBENZALDEHYDE DIETHYL ACETAL; 2 OXAZOLINYL 3,3 DIPHENYLOXIRANE; 2,3 EPOXY ALCOHOL DERIVATIVE; 2,4 TOLYLSULFINYLBENZALDEHYDE; ACETAL DERIVATIVE; ALCOHOL DERIVATIVE; BENZALDEHYDE DERIVATIVE; CARBON; ETHYLENE OXIDE DERIVATIVE; FUNCTIONAL GROUP; LITHIUM DERIVATIVE; OXIRANYLLITHIUM DERIVATIVE; SULFINYL GROUP; SULFINYLATION; SULFUR; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; LITHIATION; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 74549159211     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.12.006     Document Type: Article

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37. Crytallographic data for the structural analysis have been deposited at the Cambrigde Crystallographic data Centre, CCDC No. 749559 for the compound 5b. Copies of this information may be obtained free of charge from the Director, CCDC, 12 Union Road, Cambrigde, CB2 1FZ. UK.
38. A possible alternative kinetic resolution, with only one of the anions (3-Li or ent-3-Li) reacting with 1 in a very low stereoselective way, was readily ruled out since the recovered unreacted oxirane 4 resulted to be racemic as determined by chiral stationary phase HPLC.