ASYMMETRIC DESYMMETRIZATION OF SIGMA-SYMMETRICAL DIOLS - THE ROLE OF CHELATION IN THE DIASTEREOSELECTIVE ACETAL CLEAVAGE INDUCED BY THE CHIRAL ALPHA-SULFINYL CARBANION

Authors
MAEZAKI N SOEJIMA M SAKAMOTO A SAKAMOTO I MATSUMORI Y TANAKA T ISHIDA T IN Y IWATA C
Citation
N. Maezaki et al., ASYMMETRIC DESYMMETRIZATION OF SIGMA-SYMMETRICAL DIOLS - THE ROLE OF CHELATION IN THE DIASTEREOSELECTIVE ACETAL CLEAVAGE INDUCED BY THE CHIRAL ALPHA-SULFINYL CARBANION, Tetrahedron : asymmetry, 7(1), 1996, pp. 29-32
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
1
Year of publication
1996
Pages
29 - 32
Database
ISI
SICI code
0957-4166(1996)7:1<29:ADOSD->2.0.ZU;2-6
Abstract
The reaction mechanism of beta-elimination in alpha-sulfinyl acetals w as investigated using the chiral 3-oxo-thiochroman-1-oxide derivatives 1a and 1b. Our results show that the reaction is kinetically controll ed with the C-O bond syn to the sulfinyl oxygen being cleaved exclusiv ely. This reaction seems to proceed via six-membered ring chelation in termediates.