First transfer of chirality in the Fritsch-Buttenberg-Wiechell rearrangement, via zinc carbenoids: A migration with retention of configuration

Authors
Creton, I Rezaei, H Marek, I Normant, JF
Citation
I. Creton et al., First transfer of chirality in the Fritsch-Buttenberg-Wiechell rearrangement, via zinc carbenoids: A migration with retention of configuration, TETRAHEDR L, 40(10), 1999, pp. 1899-1902
Citations number
34
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
10
Year of publication
1999
Pages
1899 - 1902
Database
ISI
SICI code
0040-4039(19990305)40:10<1899:FTOCIT>2.0.ZU;2-L
Abstract
Carbozincation of a metallated propargylic ether can lead to a gem bismetal lic reagent with a good 1,3-diastereoselection. This latter can be relayed to a 1,4-diastereoselection, when the gembismetallic thus formed is monohal ogenated to give a carbenoid which rearranges at room temperature. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.