Premium
A Lewis Acid Catalyzed Intramolecular [4+3] Cycloaddition Route to Polycyclic Systems That Contain a Seven‐Membered Ring
Author(s) -
Prié Gildas,
Prévost Natacha,
Twin Heather,
Fernandes Stephanie A.,
Hayes Jerome F.,
Shipman Michael
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200461084
Subject(s) - cycloaddition , intramolecular force , aziridine , ring (chemistry) , lewis acids and bases , chemistry , catalysis , combinatorial chemistry , stereochemistry , organic chemistry
Two simple steps , including a new intramolecular [4+3] cycloaddition, are required for the preparation of polycycles that contain a seven‐membered ring from 2‐methyleneaziridines (see scheme). The diene component is introduced by selective lithiation/alkylation at C3 of the aziridine ring. Lewis acid catalyzed cyclization leads to the products in good yields with stereocontrol.