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Angew Chem Int Ed Engl

Title:		Preparation of Optically Enriched Secondary Alkyllithium and Alkylcopper Reagents-Synthesis of (-)-Lardolure and Siphonarienal
Author(s):		Morozova V; Skotnitzki J; Moriya K; Karaghiosoff K; Knochel P;
Address:		"Department Chemie, Ludwig-Maximilians-Universitat Munchen, Butenandtstrasse 5-13, 81377, Munchen, Germany"
Journal Title:		Angew Chem Int Ed Engl
Year:		2018
Volume:		20180330
Issue:		19
Page Number:		5516 - 5519
DOI:		10.1002/anie.201800792
ISSN/ISBN:		1521-3773 (Electronic) 1433-7851 (Linking)
Abstract:		"Optically enriched secondary alkyl iodides were converted into secondary alkyllithium and secondary alkylcopper compounds with very high retention of configuration. Quenching with various electrophiles, including chiral epoxides, provided a range of chiral molecules with high enantiomeric purity (>90 % ee). This method has been applied in an iterative fashion in the total synthesis of (-)-lardolure in 13 steps and 5.4 % overall yield (>99 % ee, dr>99:1) and siphonarienal in 15 steps and 5.6 % overall yield (>99 % ee, dr>99:1) starting from commercially available ethyl (R)-3-hydroxybutyrate (>99 % ee)"
Keywords:		asymmetric synthesis copper iterative synthesis lithium pheromone synthesis;
Notes:		"PubMed-not-MEDLINEMorozova, Varvara Skotnitzki, Juri Moriya, Kohei Karaghiosoff, Konstantin Knochel, Paul eng Research Support, Non-U.S. Gov't Germany 2018/03/08 Angew Chem Int Ed Engl. 2018 May 4; 57(19):5516-5519. doi: 10.1002/anie.201800792. Epub 2018 Mar 30"