From glycals to metal pyranosylidenes: Diastereoselective addition of electrophiles to metal carbene enolate intermediates

Authors
Jakel, C Dotz, KH
Citation
C. Jakel et Kh. Dotz, From glycals to metal pyranosylidenes: Diastereoselective addition of electrophiles to metal carbene enolate intermediates, TETRAHEDRON, 56(15), 2000, pp. 2167-2173
Citations number
70
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
15
Year of publication
2000
Pages
2167 - 2173
Database
ISI
SICI code
0040-4020(20000407)56:15<2167:FGTMPD>2.0.ZU;2-B
Abstract
Lithiated glucals react smoothly with Cr(CO)(5)THF at the metal center to g enerate the corresponding vinyl chromate intermediates which represent chro mium carbene enolate equivalents. Trapping by electrophiles provides an ent ry to novel chromium 2-deoxy-pyranosylidenes. Deuteration and allylation pr oceed with an approximately 90% d.e. in preference of the C-2-manno complex es. (C) 2000 Elsevier Science Ltd. All rights reserved.