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Induced and Non‐induced Diastereoselective Intramolecular Ene Reaction of 1,6‐Dienes: the Unusual Formation of trans ‐1,2‐Disubstituted Cyclopentanes
Author(s) -
Tietze Lutz F.,
Beifuss Uwe,
Ruther Michael,
Rühlmann Andreas,
Antel Jochen,
Sheldrick George M.
Publication year - 1988
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198811861
Subject(s) - cyclopentanes , chemistry , intramolecular force , selectivity , ene reaction , stereochemistry , asymmetric induction , medicinal chemistry , enantioselective synthesis , catalysis , organic chemistry
The formation of trans ‐1,2‐disubstituted cyclopentanes such as 2 from 1,6‐dienes such as 1 with acceptor substituents R is a remarkable process‐‐‐in the presence of ZnBr 2 the non‐induced selectivity ( trans / cis ratio) is > 96.5 :3.5 and the induced selectivity (asymmetric induction) for R′ = Me is > 99:1. Such configurated five‐membered rings are, inter alia, contained in prostaglandins and brefeldin (R′ = H, Me).