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(−)-Sparteine-mediated stereoselective intramolecular carbolithiation of alkynes

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
39
Issue
13
Identifiers
DOI: 10.1016/s0040-4039(98)00085-9
Keywords
  • Asymmetric Deprotonation
  • (−)-Sparteine
  • Intramolecular Carbolithiation
  • Alkyllithium Derivatives
  • Chiral Alkylidene Cyclopentanes

Abstract

Abstract The asymmetric deprotonation mediated by the chiral base s-butyllithium/(−)-sparteine of 4-substituted 5-hexynyl carbamates permits the synthesis of enantioenriched carbanionic pairs which undergo a regioselective 5- exo- dig ring closure with the triple bond acting as an internal electrophile. The functionalized five-membered rings are formed with complete stereoselectivity in high yields.

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