DIASTEREOSELECTIVITY IN THE PREPARATION OF 4-PHENYLTHIO-4-BUTANOLIDE DERIVATIVES BY THE USE OF THE PUMMERER REARRANGEMENT

Authors
SU HW HIWATARI Y SOENOSAWA M SASUGA K SHIRAI K KUMAMOTO T
Citation
Hw. Su et al., DIASTEREOSELECTIVITY IN THE PREPARATION OF 4-PHENYLTHIO-4-BUTANOLIDE DERIVATIVES BY THE USE OF THE PUMMERER REARRANGEMENT, Bulletin of the Chemical Society of Japan, 66(9), 1993, pp. 2603-2611
Citations number
7
Categorie Soggetti
Chemistry
Journal title
Bulletin of the Chemical Society of Japan → ACNP
ISSN journal
00092673
Volume
66
Issue
9
Year of publication
1993
Pages
2603 - 2611
Database
ISI
SICI code
0009-2673(1993)66:9<2603:DITPO4>2.0.ZU;2-#
Abstract
Diastereoselectivity in the preparation of 4-phenylthio-4-butanolide d erivatives by the Pummerer rearrangement of 4-phenylsulfinylbutanoic a cid derivatives was clarified. The reaction of 3-alkyl-4-phenylsulfiny lbutanoic acid with acetic anhydride resulted in the predominant forma tion of trans-3-alkyl-4-phenylthio-4-butanolide. Lactonization of 2,3- dialkyl-4-phenylsulfinylbutanoic acid gave (2RS,3RS, 4SR)-2,3-dialkyl- 4-phenylthio-4-butanolide predominantly.