The use of (-)-8-phenylisoneomenthol and (-)-8-phenylmenthol in the enantioselective synthesis of 3-functionalized 2-azabicyclo[2.2.1]heptane derivatives via aza-Diels-Alder reaction

• Type: Article in International Scientific Journal
• Date: 2006

Authors

Maria Luisa C Cardoso do Vale (Author) FCUP; Jos Enrique Rodriguez Borges (Author) FCUP; Olga Caamano (Author) Other; Franco Fernandez (Author) Other; Xerardo Garcia Mera (Author) Other

Journal

Title: Tetrahedron

Vol. 62

Pages: 9475-9482

ISSN: 0040-4020

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 25 Citations

Scopus - 27 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

CORDIS: Physical sciences > Chemistry > Organic chemistry

Other information

Authenticus ID: P-004-GNM

DOI: 10.1016/j.tet.2006.06.118

Abstract (EN): The asymmetric aza-Diels-Alder reaction of the (1R)-8-phenylmenthyl or (1R)-8-phenylisoneomenthyl glyoxylate-derived N-benzylimine with cyclopentadiene resulted in the enantioselective synthesis of the corresponding pure [(1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-ene]-3-carboxylates (80 or 69% yield, respectively). Reduction of these cycloadducts with LiAlH4 afforded pure (-)-[(1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-en-3-yl] methanol. Furthermore, a reaction sequence based on Barbier-Wieland degradation of both (1S,3-exo)-adducts afforded pure (+)-(1R)-2-benzoyl-2-azabicyclo[2.2.1]heptan-3-one. In the course of the two transformation sequences referred, the chiral auxiliaries were recovered in a virtually quantitative way.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 8