Reversal of regioselection in the rearrangement of cinnamate diol cyclic iminocarbonates

Authors
Cho, GY Park, JN Ko, SY
Citation
Gy. Cho et al., Reversal of regioselection in the rearrangement of cinnamate diol cyclic iminocarbonates, TETRAHEDR L, 41(11), 2000, pp. 1789-1792
Citations number
7
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
11
Year of publication
2000
Pages
1789 - 1792
Database
ISI
SICI code
0040-4039(20000311)41:11<1789:RORITR>2.0.ZU;2-Y
Abstract
The rearrangement of cinnamate diol cyclic iminocarbonates can be regiosele ctively controlled by using, as the nucleophile, Bu4NBr (for beta[benzylic] -nitrogen regioselection) or LiI (for the alpha-nitrogen isomers). This dis covery will expand the synthetic utilities of the cyclic iminocarbonate rea rrangement and the asymmetric dihydroxylation processes. (C) 2000 Elsevier Science Ltd. All rights reserved.