A new strategy for the stereoselective synthesis of 1,2,3-trisubstituted cyclopropanes

Boehm, Claudius and Schinnerl, Marina and Bubert, Christian and Zabel, Manfred and Labahn, Thomas and Parisini, Emilio and Reiser, Oliver (2000) A new strategy for the stereoselective synthesis of 1,2,3-trisubstituted cyclopropanes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (16). pp. 2955-2965. ISSN 1434-193X

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Abstract

The stereoselective synthesis of highly functionalized 1,2,3-trisubstituted cyclopropanes 1 and 2, starting from readily available furans 3 or N-protected pyrrole 4, is described. Furthermore, exceptionally high diastereocontrol in agreement with the Felkin-Anh model was observed for the addition of nucleophiles to the title compounds.

Item Type: Article
Uncontrolled Keywords: CONFORMATIONALLY RESTRICTED ANALOGS; SIMMONS-SMITH REACTION; ALLYLIC ALCOHOLS; ENANTIOSELECTIVE CYCLOPROPANATION; ASYMMETRIC CYCLOPROPANATION; ENANTIOMERICALLY PURE; RING-SYSTEM; SUBSTITUTED CYCLOPROPANES; BIOLOGICAL-ACTIVITY; CHIRAL LIGANDS; aldol reactions; amino aldehydes; donor-acceptor cyclopropanes; Felkin-Anh rule; nucleophilic additions
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Depositing User: Dr. Gernot Deinzer
Date Deposited: 29 Mar 2022 09:25
Last Modified: 29 Mar 2022 09:25
URI: https://pred.uni-regensburg.de/id/eprint/42294

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