Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 9, Pages 2754-2757Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201409165
Keywords
carbanions; diastereoselectivity; kinetics; lithiation; nucleophilic substitution
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Funding
- Deutsche Forschungsgemeinschaft [SFB 749]
- Deutscher Akademischer Austauschdienst
- Alexander von Humboldt-Stiftung
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Secondary alkyllithium reagents bearing an OTBS group (TBS=tert-butyldimethylsilyl) at the 3-position can be prepared stereoconvergently through an I/Li exchange from a diastereomeric mixture of the corresponding secondary alkyl iodides. These lithium reagents react with a range of electrophiles, including carbon electrophiles, with retention of configuration to yield various 1,3-difunctionalized derivatives with good diastereoselectivities. Kinetic studies show that the 3-siloxy group strongly accelerates the epimerization at the lithium-substituted carbon atom. This method offers a new way to construct chiral open-chain molecules with excellent stereoselectivity.
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