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Synfacts 2011(7): 0729-0729  
DOI: 10.1055/s-0030-1260612
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Reactivity under Control

Contributor(s): Timothy M. Swager, Shuang Liu
D. Conreaux, N. Mehanna, C. Herse, J. Lacour*
University of Geneva, Switzerland
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Publication History

Publication Date:
17 June 2011 (online)

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Significance

Highly stable quinacridinium derivatives 1 are transformed into reactive carbanions 3 by consecutive reduction and metalation. Intermediates 3 react readily with electrophiles, such as isothiocyanates, acid anhydrides, and hexyl ­iodide. Complete configuration retention has been proved by reacting (+)-2a with n-BuLi followed by benzyl isothiocyanate or methanol-d 4.