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Synthesis of Substituted Oxa- and Aza[3.2.1] and [4.3.1]Bicyclics via an Unprecedented Molybdenum-Mediated 1,5-“Michael-Type” Reaction

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posted on 2005-08-17, 00:00 authored by Yongqiang Zhang, Lanny S. Liebeskind
The direct internal nucleophilic functionalization of a π-bound carbon of neutral TpMo(CO)2(5-oxo-η3-pyranyl) and TpMo(CO)2(5-oxo-η3-pyridinyl) complexes by enolates represents a new reaction profile for neutral TpMo(CO)23-allyl) complexes. This Mo-mediated “1,5-Michael reaction” proceeds in good to excellent yields and provides, after demetalation, a new and efficient synthetic approach to oxa- and aza[3.2.1]bicyclics of high enantiomeric purity.