Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 37, Pages 10963-10967Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201505740
Keywords
configurational stability; copper; diastereoselectivity; lithium; zinc
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Funding
- DAAD
- [SFB 749 B2]
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Functionalized secondary alkyllithium reagents obtained by I/Li exchange from the corresponding secondary alkyl iodides undergo two successive transmetalations with Me3SiCH2ZnBrLiBr and CuBr2LiClMe(2)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 LaCl(3)2LiCl 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.
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