A proline-catalyzed asymmetric Robinson annulation reaction

Authors
Bui, T Barbas, CF
Citation
T. Bui et Cf. Barbas, A proline-catalyzed asymmetric Robinson annulation reaction, TETRAHEDR L, 41(36), 2000, pp. 6951-6954
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
36
Year of publication
2000
Pages
6951 - 6954
Database
ISI
SICI code
0040-4039(20000902)41:36<6951:APARAR>2.0.ZU;2-K
Abstract
A single-step enantioselective synthesis of the Wieland-Miescher ketone (5) is presented. We show that L-proline as well as a number of other chiral a mines can act as catalysts of both steps of the Robinson annulation reactio n. Other chiral amines are identified as catalysts of Michael and aldol add ition reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.