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(-)-Sparteine-mediated metalation of ferrocenesulfonates. The first case of double asymmetric induction of ferrocene planar chirality. | LitMetric
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(-)-Sparteine-mediated metalation of ferrocenesulfonates. The first case of double asymmetric induction of ferrocene planar chirality.

Costa Metallinos Victor Snieckus

Org Lett

Department of Chemistry, Queen's University, Kingston, ON, K7L 3N6, Canada.

Published: May 2002

[reaction: see text] A new process for induction of planar chirality via a matched chiral-directed metalation group (DMG)/(-)-sparteine interaction is demonstrated. Thus, s-BuLi metalation of (-)-menthylferrocenesulfonate (8b) with (-)-sparteine constitutes a matched pair resulting in amplification of the dr in the 2-formyl product 10a.

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http://dx.doi.org/10.1021/ol025963cDOI Listing

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