Synthesis of 7-azabicyclo[2.2.1]heptanes by anionic cyclization

Authors
Coldham, I Fernandez, JC Snowden, DJ
Citation
I. Coldham et al., Synthesis of 7-azabicyclo[2.2.1]heptanes by anionic cyclization, TETRAHEDR L, 40(9), 1999, pp. 1819-1822
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
9
Year of publication
1999
Pages
1819 - 1822
Database
ISI
SICI code
0040-4039(19990226)40:9<1819:SO7BAC>2.0.ZU;2-B
Abstract
Cyclizations of alpha-amino-organolithiums, derived by tin-lithium exchange , which proceed via a stereoselective two-electron process and totally regi ospecific 5-exo-trig ring closure, have been extended to the preparation of the 7-azabicyclo[2.2.1]heptane ring system. Cyclization occurs from either the cis or the trans isomer of 5-allyl-2-tri-n-butylstannyl-N-benzylpyrrol idine to give only the exo product as a single diastereomer in isolated yie lds up to 83%. (C) 1999 Elsevier Science Ltd. All rights reserved.