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Intramolecular Allylsilane Addition to Chiral Alkylidene‐1,3‐dicarbonyl Compounds for the Synthesis of Enantiomerically Pure trans ‐1,2‐Disubstituted Cyclopentanes and Cyclohexanes
Author(s) -
Tietze Lutz F.,
Schünke Christian
Publication year - 1995
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.199517311
Subject(s) - cyclopentanes , cyclohexanes , stereocenter , chemistry , lewis acids and bases , stereochemistry , organic chemistry , enantioselective synthesis , catalysis
Three new stereogenic centers characterize the 1,2‐ trans ‐disubstituted cyclopentanes 2a and cyclohexanes 2b , which can be prepared enantiomerically pure with the Lewis acid SnCl 4 in a highly selective SnCl 4 ‐induced cyclization of the chiral alkylidene malonic acid derivatives 1a and 1b , respectively. The chiral auxiliary can be removed from 2 with LiAlH 4 .