4-PENTENESELENOTHIOIC ACID S-ALKYL ESTERS - SYNTHESIS VIA THE SELENO-CLAISEN REARRANGEMENT

Authors
MURAI T TAKADA H KAKAMI K FUJII M MAEDA M KATO S
Citation
T. Murai et al., 4-PENTENESELENOTHIOIC ACID S-ALKYL ESTERS - SYNTHESIS VIA THE SELENO-CLAISEN REARRANGEMENT, Tetrahedron, 53(36), 1997, pp. 12237-12247
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
36
Year of publication
1997
Pages
12237 - 12247
Database
ISI
SICI code
0040-4020(1997)53:36<12237:4ASE-S>2.0.ZU;2-J
Abstract
Selenothioic acid S-alkyl esters were reacted with allylic bromides in the presence of Et3N. Mono-, di- or tri-allylated products were selec tively formed by changing reaction temperatures. limes and allylic bro mides used. The reaction proceeded with high regio- and stereoselectiv ity via the seleno-Claisen rearrangement. The selective synthesis of m ono-allylated esters was also attained by the reaction of in-situ gene rated lithium eneselenolates with allylic bromides. (C) 1997 Elsevier Science Ltd.