Diastereoselective alpha-iminoamine rearrangement: asymmetric synthesis of(R)-(-)- and (S)-(+)-2-benzyl-2-hydroxycyclohexanone

Authors
Bisel, P Lauktien, G Weckert, E Frahm, AW
Citation
P. Bisel et al., Diastereoselective alpha-iminoamine rearrangement: asymmetric synthesis of(R)-(-)- and (S)-(+)-2-benzyl-2-hydroxycyclohexanone, TETRAHEDR-A, 9(22), 1998, pp. 4027-4034
Citations number
24
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
9
Issue
22
Year of publication
1998
Pages
4027 - 4034
Database
ISI
SICI code
0957-4166(19981127)9:22<4027:DARASO>2.0.ZU;2-U
Abstract
A convenient asymmetric synthesis of both (R)-(-)- and (S)-(+)-2-benzyl-2-h ydroxycyclohexanones starting from racemic 2-benzyloxycyclohexanone and the chiral auxiliary 1-phenylethylamine is reported. The route involves a [1,3 ]-sigmatropic shift and a new diastereoselective alpha-iminoamine rearrange ment of a 2-benzyl-2-iminocyclohexanamine substrate. (C) 1998 Elsevier Scie nce Ltd. All rights reserved.