Enantioselective synthesis of each stereoisomer of the pyranoid linalool oxides: the geraniol route

Authors
Vidari, G Di Rosa, A Castronovo, F Zanoni, G
Citation
G. Vidari et al., Enantioselective synthesis of each stereoisomer of the pyranoid linalool oxides: the geraniol route, TETRAHEDR-A, 11(4), 2000, pp. 981-989
Citations number
38
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
4
Year of publication
2000
Pages
981 - 989
Database
ISI
SICI code
0957-4166(20000310)11:4<981:ESOESO>2.0.ZU;2-R
Abstract
Each of the four enantiomerically pure tetrahydropyran linalool oxides was synthesized by an acid-catalyzed cyclization of an appropriate epoxy-alcoho l obtained by consecutive Sharpless dihydroxylation (AD) and epoxidation (A E) reactions of geraniol derivatives. An interesting example of double asym metric induction was observed during the AE of a bis(homoallylic) N-naphthy lcarbammae. (C) 2000 Elsevier Science Ltd. All rights reserved.