A New Strategy for the Stereoselective Synthesis of 1,2,3-trisubstituted Cyclopropanes

Böhm, 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. Eur. J. Org. Chem. 2000 (16), pp. 2955-2965.

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Other URL: http://dx.doi.org/10.1002/1099-0690(200008)2000:16<2955::AID-EJOC2955>3.0.CO;2-3

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
Institutions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Identification Number:
ValueType
10.1002/1099-0690(200008)2000:16<2955::AID-EJOC2955>3.0.CO;2-3DOI
Keywords:Aldol reactions; Amino aldehydes; Donor-acceptor cyclopropanes; Felkin-Anh rule; Nucleophilic additions
Subjects:500 Science > 540 Chemistry & allied sciences
Status:Published
Refereed:Yes, this version has been refereed
Created at the University of Regensburg:Unknown
Owner:Helge Knüttel (ADMIN)
Deposited On:29 Aug 2006
Last Modified:05 Aug 2009 15:22
Item ID:314
Owner Only: item control page