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Publication 191  


  1. “Asymmetric Dearomatization with Chiral Auxiliaries and Reagents”
    E.P. Kündig,
    in Asymmetric Dearomatization Reactions; S.-L. You (Ed.); Wiley-VCH Verlag: Weinheim, Germany; Chapter 2; p. 9-31.

This chapter reviews dearomatization reactions of benzene as well as substituted and fused analogs with chiral auxiliaries and chiral reagents. It is organized according to the source of chiral information leading to enantiomerically or diastereomerically enriched alicyclic products. In the course of the pioneering work of Meyers and coworkers in developing oxazolines as auxiliaries, the directing power of this heterocycle was probed in the ortho-lithiation/ortho-substitution of phenyl oxazolines and ortho-chloro and methoxy analogs, respectively. Stereogenic centers, chiral auxiliaries, ligands, and planar chiral complexes provide a vast array of methods to obtain functionalized nonracemic alicyclic products from aromatics. Reactions range from those that are purely of mechanistic interests to those that await further optimizations and to those that provide very powerful asymmetric transformations for organic synthesis. While stoichiometric in chiral information, many reactions provide better solutions for asymmetric dearomatizations and the field is bound to see further development.

DOI : 10.1002/9783527698479.ch2