Stereoselektive Synthese von 3‐substituierten Cyclobutanolen und Folgeprodukten | Zendy

Dehmlow Eckehard V. | Zendy; Büker Sabine | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research