Stereoselective Retentive Domino Transmetalations of Secondary Alkyllithium Compounds to Functionalized Secondary Alkylcopper Reagents

Autor:	Meike Simon, Kohei Moriya, Konstantin Karaghiosoff, Rasmus Mose, Paul Knochel
Rok vydání:	2015
Předmět:	chemistry.chemical_classification Allylic rearrangement Ethylene oxide Chemistry General Chemistry Catalysis law.invention Solvent chemistry.chemical_compound law Reagent Electrophile Organic chemistry Stereoselectivity Walden inversion Alkyl
Zdroj:	Angewandte Chemie International Edition. 54:10963-10967
ISSN:	1433-7851
DOI:	10.1002/anie.201505740
Popis:	Functionalized secondary alkyllithium reagents obtained by I/Li exchange from the corresponding secondary alkyl iodides undergo two successive transmetalations with Me3 SiCH2 ZnBr⋅LiBr and CuBr⋅2 LiCl⋅Me2 S to provide functionalized secondary alkylcopper compounds with high retention of configuration. These alkylcopper derivatives react further with electrophiles such as alkynyl esters, acid chlorides, allylic chlorides, ketals, ethylene oxide, and 3-iodocyclopentanone with high retention of configuration. A related sequence of transmetalations with MeMgI and LaCl3 ⋅2 LiCl allows a retentive addition of secondary alkyllithium reagents to acetone. The influence of the solvent on the configurational stability of secondary alkylzinc reagents is described.
Databáze:	OpenAIRE
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