ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF ALL 4 POSSIBLE STEREOISOMERS OF 2-(PHENYLHYDROXYMETHYL)QUINUCLIDINE

Authors
LYGO B CROSBY J LOWDON TR WAINWRIGHT PG
Citation
B. Lygo et al., ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF ALL 4 POSSIBLE STEREOISOMERS OF 2-(PHENYLHYDROXYMETHYL)QUINUCLIDINE, Tetrahedron letters, 38(13), 1997, pp. 2343-2346
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
13
Year of publication
1997
Pages
2343 - 2346
Database
ISI
SICI code
0040-4039(1997)38:13<2343:EADSOA>2.0.ZU;2-L
Abstract
An enantio- and diastereoselective synthesis of all four possible ster eoisomers of 2-(phenylhydroxymethyl)quinuclidine is reported. Key step s involve the use of the Sharpless dihydroxylation protocol to induce asymmetry, and stereodivergent cyclisations of the resulting diol to f orm the quinuclidine ring. (C) 1997 Elsevier Science Ltd.