Stereoselective synthesis and reactions of secondary alkyllithium reagents functionalized at the 3-position

Kohei Moriya, Dorian Didier, Meike Simon, Jeffrey M. Hammann, Guillaume Berionni, Konstantin Karaghiosoff, Hendrik Zipse, Herbert Mayr, Paul Knochel, K. Moriya, D. Didier, M. Simon, J. M. Hammann, Guillaume Berionni, Prof K. Karaghiosoff, Prof H. Zipse, Prof H. Mayr, Prof P. Knochel

Résultats de recherche: Contribution à un journal/une revueArticleRevue par des pairs

Résumé

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.

langue originaleAnglais
Pages (de - à)2754-2757
Nombre de pages4
journalAngewandte Chemie - International Edition
Volume54
Numéro de publication9
Les DOIs
Etat de la publicationPublié - 23 févr. 2015
Modification externeOui

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