A SHORT ENANTIOSELECTIVE ACCESS TO 2,3,6-TRIALKYLPIPERIDINES AND 5,8-DIALKYLINDOLIZIDINES

Authors
WONG YS GNECCO D MARAZANO C CHIARONI A RICHE C BILLION A DAS BC
Citation
Ys. Wong et al., A SHORT ENANTIOSELECTIVE ACCESS TO 2,3,6-TRIALKYLPIPERIDINES AND 5,8-DIALKYLINDOLIZIDINES, Tetrahedron, 54(32), 1998, pp. 9357-9372
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
32
Year of publication
1998
Pages
9357 - 9372
Database
ISI
SICI code
0040-4020(1998)54:32<9357:ASEAT2>2.0.ZU;2-N
Abstract
An enantioselective access to 2,3,6-trialkylpiperidines 5 is described . This sequence is illustrated by the four-step syntheses, from salts 1, of piperidine 6 and indolizidines 7 and 8. The overall yields are i n the range 10-15%. The stereochemistry of intermediates is discussed, supported by two X-ray studies, and comparison with analogs. Stereoch emical properties of intermediate oxazolidine derivatives 4 were used to orient the syntheses towards different diastereoisomers such as 7 o r 8. (C) 1998 Elsevier Science Ltd. All rights reserved.