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Stereoselektive Synthese von 3‐substituierten Cyclobutanolen und Folgeprodukten
Author(s) -
Dehmlow Eckehard V.,
Büker Sabine
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931261228
Subject(s) - chemistry , stereoselectivity , mitsunobu reaction , alkene , selectivity , stereochemistry , halogenation , organic chemistry , catalysis
Stereoselective Synthesis of 3‐Substituted Cyclobutanols and Products Derived Therefrom 3‐Substituted cyclobutanones 2 are prepared by alkene/dichloroketene cycloadditions and subsequent dehalogenation. Reduction with LiAlH(O t Bu) 3 furnishes cis ‐cyclobutanols 3 in 95–100% selectivity. Mitsunobu inversion turned out to be the only practical method to get trans isomers 4 in high selectivity. A stereoselective cyclobutanol→bromocyclobutane conversion could be achieved only by a modified Mitsunobu reaction. Cross coupling between zinc derivatives of bromocyclobutanes 9 and aromatic bromides is not stereoselective.