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Financial support of this work by the Ministerio de Educación y Ciencia (CTQ2006-06741/BQU) is gratefully acknowledged. V.M. thanks Ministerio de Educación y Ciencia for a predoctoral fellowship.
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Communication
Configurational Control of Benzyl Carbanion–Copper Complexes by Sulfinyl Groups: Synthesis of Optically Pure Allenes with Central and Axial Chirality†
Article first published online: 25 JUL 2008
DOI: 10.1002/anie.200802158
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
García Ruano, J., Marcos, V. and Alemán, J. (2008), Configurational Control of Benzyl Carbanion–Copper Complexes by Sulfinyl Groups: Synthesis of Optically Pure Allenes with Central and Axial Chirality. Angew. Chem. Int. Ed., 47: 6836–6839. doi: 10.1002/anie.200802158
- †
Publication History
- Issue published online: 20 AUG 2008
- Article first published online: 25 JUL 2008
- Manuscript Received: 8 MAY 2008
Funded by
- Ministerio de Educación y Ciencia. Grant Number: CTQ2006-06741/BQU
Keywords:
- allenes;
- chirality;
- copper;
- sulfinyl groups;
- synthetic methods
Lean, mean, chiral allene: Optically pure complexes 2 react with propargyl bromides and mesylates 1 to afford the title products (see scheme; LG=leaving group). The regioselectivity and the configuration of the chiral axis are completely controlled, and the stereoselectivity at the benzylic position is high. Kinetic resolution of racemic propargyl mesylates can also be achieved with these reagents.