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Synlett 2000; 2000(7): 0950-0954
DOI: 10.1055/s-2000-6648
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Asymmetric Lithiation of an Allyl Carbamate Induced by a Complexing Remote Chiral Substituent

Dirk K. Heimbach* , Roland Fröhlich, Birgit Wibbeling, Dieter Hoppe
  • *Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, 48149 Münster, Germany; Fax + 49(2 51)8 33 97 72; E-mail: dhoppe@uni-muenster.de
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Publikationsdatum:
31. Dezember 2000 (online)

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The stereohomogeneous (δ-arenesulfonyloxazolidine)-substituted allyl carbamate 7, after lithiation under several conditions, forms the lithium compound 8 with high diastereoselectivity (dr > 97 : 3). 8 is trapped with a number of electrophiles to give the diastereo- and enantiomerically enriched α- and γ-substitution products. Evidence is contributed for: i) 8 is configurationally unstable and the relative configuration is thermodynamically controlled by chelation with the chiral auxiliary, ii) substitution in the α-position proceeds with inversion of the configuration.

chiral allyllithium compounds - stereochemistry of the electrophilic substitution - stannylation - lithiodestannylation - chiral N-sulfonyl-1,3-oxazolidines