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Chemistry


Title:"Stereoselective Synthesis and Retentive Trapping of alpha-Chiral Secondary Alkyllithiums Leading to Stereodefined alpha,beta-Dimethyl Carboxylic Esters"
Author(s):Morozova V; Moriya K; Mayer P; Knochel P;
Address:"Department Chemie, Ludwig-Maximilians-Universitat Munchen, Butenandtstrasse 5-13, 81377, Munchen, Germany. Department Chemie, Ludwig-Maximilians-Universitat Munchen, Butenandtstrasse 5-13, 81377, Munchen, Germany. Paul.Knochel@cup.uni-muenchen.de"
Journal Title:Chemistry
Year:2016
Volume:20160608
Issue:29
Page Number:9962 - 9965
DOI: 10.1002/chem.201601911
ISSN/ISBN:1521-3765 (Electronic) 0947-6539 (Linking)
Abstract:"The treatment of alpha-chiral secondary alkyl iodides with tBuLi at -100 degrees C leads to the corresponding secondary alkyllithiums with high retention of configuration. Subsequent quenching with various electrophiles such as Bu2 S2 , DMF, MeOB(OR)2 , or Et2 CO provides the desired products with retention of configuration. Furthermore, a transmetalation with CuBr?naP(OEt)3 also allows retentive trapping with acid chlorides and ethylene oxide. The quenching of the resulting alkyllithiums with ClCO2 Et furnishes stereoselectively syn- and anti-ethyl-2,3-dimethyl ester carboxylates (d.r.>94 %). Related esters bearing three adjacent stereo-controlled centers (stereotriads) have also been prepared. This method has been applied to the synthesis of the ant pheromone (+/-)-lasiol in 26 % overall yield (four steps) with d.r.=97:3 starting from commercially available cis-2,3-epoxybutane"
Keywords:carboxylic acids copper lithium pheromone stereotriads;
Notes:"PubMed-not-MEDLINEMorozova, Varvara Moriya, Kohei Mayer, Peter Knochel, Paul eng Germany 2016/05/04 Chemistry. 2016 Jul 11; 22(29):9962-5. doi: 10.1002/chem.201601911. Epub 2016 Jun 8"

 
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