Enantioselective protonation/diastereoselective reduction with sodium naphthalenide-acetamide; A new synthesis of chiral trans-2-phenylcyclohexanol

Authors
Asensio, G Cuenca, A Gavina, P Medio-Simon, M
Citation
G. Asensio et al., Enantioselective protonation/diastereoselective reduction with sodium naphthalenide-acetamide; A new synthesis of chiral trans-2-phenylcyclohexanol, TETRAHEDR L, 40(20), 1999, pp. 3939-3940
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
20
Year of publication
1999
Pages
3939 - 3940
Database
ISI
SICI code
0040-4039(19990514)40:20<3939:EPRWSN>2.0.ZU;2-M
Abstract
An efficient synthesis of trans-2-phenylcyclohexanol has been achieved by e nantioselective protonation of the enolate of 2-phenylcyclohexanone with al pha-sulfinyl alcohols and subsequent reduction of the chiral ketone hy sodi um naphthalenide in the presence of acetamide. Interestingly. the chirality source is not consumed in the synthesis of the chiral target. (C) 1999 Els evier Science Ltd. All rights reserved.