Boron azaenolates of chiral oxazolines: synthesis of optically active formyl oxiranes

Authors
Florio, S Capriati, V Luisi, R Abbotto, A
Citation
S. Florio et al., Boron azaenolates of chiral oxazolines: synthesis of optically active formyl oxiranes, TETRAHEDR L, 40(41), 1999, pp. 7421-7425
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
41
Year of publication
1999
Pages
7421 - 7425
Database
ISI
SICI code
0040-4039(19991008)40:41<7421:BAOCOS>2.0.ZU;2-D
Abstract
Boron azaenolates 2 and 8 from the optically active chloromethyloxazolines 1 and 7 have been found to couple with ketones in a highly diastereoselecti ve fashion, which depends markedly upon the geometry (Z) of the azaenolates and the nature of the ligands which are present on the boron atom, in good accordance with semiempirical calculations (AM1). (C) 1999 Elsevier Scienc e Ltd. All rights reserved.