Enantioselective synthesis of [(1R,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5en-3-yl] methanol via Aza-Diels-Alder reaction

• Type: Article in International Scientific Journal
• Date: 2005

Authors

Fernandez, F (Author) Other; Garcia Mera, X (Author) Other; Vale, MLC (Author) FCUP; Rodriguez Borges, JE (Author) FCUP

Journal

Title: Synlett

Pages: 319-321

ISSN: 0936-5214

Publisher: Thieme

Indexing

ISI Web of Knowledge - 16 Citations

Scopus - 20 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-000-4ZB

DOI: 10.1055/s-2004-836068

Abstract (EN): The asymmetric aza-Diels-Alder reaction of the 8-phenylneomenthyl (or 8-phenylisomenthyl) glyoxylate-derived N-benzylimine with cyclopentadiene resulted in the enantioselective synthesis of the corresponding [(1R,3-evo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-en-3-yl]carboxylate. In both cases, the (1R,3-exo)-adduct was the main diastereomer and was isolated in 70% and 65% yield, respectively. Reduction of the (1R,3-exo)-adducts with LiAlH4 afforded [(1R,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-en-3-yl] methanol, with recovery of the chiral auxiliaries with retention of configuration.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 3