Forming tertiary organolithiums and organocuprates from nitrile precursors and their bimolecular reactions with carbon electrophiles to form quaternary carbon stereocenters
- Schnermann, M.J. 1
- Untiedt, N.L. 1
- Jiménez-Osés, G. 2
- Houk, K.N. 2
- Overman, L.E. 1
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1
University of California, Irvine
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2
University of California Los Angeles
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ISSN: 1433-7851
Año de publicación: 2012
Volumen: 51
Número: 38
Páginas: 9581-9586
Tipo: Artículo
Otras publicaciones en: Angewandte Chemie International
Resumen
Unstabilized tertiary organolithium intermediates are conveniently generated by reductive decyanation of nitriles, and these reagents and their derived cuprates couple in useful yields with carbon- centered electrophiles (see example). Chiral tertiary organolithium and organocuprate derivatives of substituted cis-perhydroazulenes and cis-perhydropentalenes react with electrophiles with high diastereoselectivity from the more-hindered concave face. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.