ENANTIOSELECTIVE SYNTHESIS OF ALPHA-HYDROXY THIOESTERS VIA OXAZABOROLIDINE-MEDIATED REDUCTION OF ALPHA-PHENYLTHIO ENONES

Authors
BERENGUER R CAVERO M GARCIA J MUNOZ M
Citation
R. Berenguer et al., ENANTIOSELECTIVE SYNTHESIS OF ALPHA-HYDROXY THIOESTERS VIA OXAZABOROLIDINE-MEDIATED REDUCTION OF ALPHA-PHENYLTHIO ENONES, Tetrahedron letters, 39(15), 1998, pp. 2183-2186
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
15
Year of publication
1998
Pages
2183 - 2186
Database
ISI
SICI code
0040-4039(1998)39:15<2183:ESOATV>2.0.ZU;2-X
Abstract
alpha-Phenylthio-alpha,beta-alkenones (2), readily available by Pd(II) -catalysed coupling of (E)-1-phenylthio-1-tributylstannylhex-1-ene wit h the corresponding acid chlorides, have been treated with borane in t he presence of phenylglycine- or proline-derived oxazaborolidines to a fford 2-phenylthio-2-alken-1-ols (3) with good to excellent enantiosel ectivities. Ozonolysis of 3 provides a new and efficient route to chir al a-hydroxy thioesters 4. (C) 1998 Elsevier Science Ltd. All rights r eserved.