Chiral dipole-stabilized anions: experiment and theory in benzylic and allylic systems. Stereoselective deprotonations, pyramidal inversions, and stereoselective …

…, M Goicoechea-Pappas, TV Anklekar…

Index: Rein, Kathleen; Goicoechea-Pappas, Marta; Anklekar, Tarakeshwar V.; Hart, Georgina C.; Smith, Gregory A.; Gawley, Robert E. Journal of the American Chemical Society, 1989 , vol. 111, # 6 p. 2211 - 2217

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Citation Number: 73

Abstract

Abstract: The stereoselective alkylation of chiral (tetrahydroisoquinoly1) oxazolines has been investigated. We report the details of this investigation, including an examination of the effect of both temperature and oxazoline substituent structure on the alkylation diastereoselectivity, a comparison of monodentate vs bidentate chelation of the organolithium, an evaluation of the effect of solvent and chelating solvent additives, the ...

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