Induced and Non‐induced Diastereoselective Intramolecular Ene Reaction of 1,6‐Dienes: the Unusual Formation of  trans ‐1,2‐Disubstituted Cyclopentanes | Zendy

Tietze Lutz F. | Zendy; Beifuss Uwe | Zendy; Ruther Michael | Zendy; Rühlmann Andreas | Zendy; Antel Jochen | Zendy; Sheldrick George M. | Zendy

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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).

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