Stereoselective synthesis of polyhydroxylated pyrrolidines: a route to novel 3,5-bis(hydroxymethyl)pyrrolidines from 2-azabicyclo[2.2.1]hept-5-enes

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

Authors

Jose J Alves (Author) Other; Xerardo Garcia Mera (Author) Other; Luisa L C Vale (Author) FCUP; Teresa P Santos (Author) Other; Fabio R Aguiar (Author) Other; Jose E Rodriguez Borges (Author) FCUP

Journal

Title: Tetrahedron Letters

Vol. 47

Pages: 7595-7597

ISSN: 0040-4039

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 19 Citations

Scopus - 18 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-004-GHV

DOI: 10.1016/j.tetlet.2006.08.077

Abstract (EN): An efficient preparation of racemic and chiral 2-functionalized-3,5-bis(hydroxymethyl)pyrrolidines is described. The method uses 2-azabicyclo[2.2.1]hept-5-enes, readily obtained from glyoxylates of aliphatic amines and cyclopentadiene, as starting material, The hydroxylation of the double bond followed by the oxidative cleavage of the six-membered ring and in situ reduction of the dialdehyde intermediate gives the title pyrrolidines.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 3