Organometallic Enantiomeric Scaffolding: General Access to 2-Substituted Oxa-and Azabicyclo [3.2. 1] octenes via a Brønsted Acid Catalyzed [5+ 2] Cycloaddition …

EC Garnier, LS Liebeskind

Index: Garnier, Ethel C.; Liebeskind, Lanny S. Journal of the American Chemical Society, 2008 , vol. 130, # 23 p. 7449 - 7458

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Citation Number: 36

Abstract

6-Substituted TpMo (CO) 2 (η-2, 3, 4-pyranyl)-and TpMo (CO) 2 (η-2, 3, 4-pyridinyl) scaffolds (Tp= hydridotrispyrazolylborato) function as reaction partners in an efficient regio-and stereocontrolled synthesis of functionalized oxa-and azabicyclo [3.2. 1] octenes through a novel Brønsted acid catalyzed [5+ 2] cycloaddition reaction. Excellent exo-selectivities are obtained, and the reaction gives products with complete retention of enantiomeric purity ...