THE THIOPYRAN ROUTE TO POLYPROPIONATES REVISITED - SELECTIVE SYN AND ANTI ALDOL REACTIONS VIA 3,6-DIHYDRO-4-TRIMETHYLSILYLOXY-2H-THIOPYRAN

Authors
WARD DE MAN CC GUO C
Citation
De. Ward et al., THE THIOPYRAN ROUTE TO POLYPROPIONATES REVISITED - SELECTIVE SYN AND ANTI ALDOL REACTIONS VIA 3,6-DIHYDRO-4-TRIMETHYLSILYLOXY-2H-THIOPYRAN, Tetrahedron letters, 38(13), 1997, pp. 2201-2202
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
13
Year of publication
1997
Pages
2201 - 2202
Database
ISI
SICI code
0040-4039(1997)38:13<2201:TTRTPR>2.0.ZU;2-6
Abstract
Aldol reaction of the amine free Li enolate of tetrahydro-4H-thiopyran -4-one with 1,4-dioxa-8-thiaspiro[4.5]decane-6-carboxaldehyde gives ma inly the 2,3-anti-3,4-syn aldol(7:1) in good yield; reaction of the LD A generated lithium enolate proceeds poorly. Using the trimethylsilyl enol ether and TiCl4 gives the 2,3-syn-3,4-syn aldol(>10:1). The adduc ts can be used for polypropionate synthesis. (C) 1997 Elsevier Science Ltd.