The first examples of catalytic enantioselective ring-opening/cross-metathesis (EROCM) reactions with enol ethers are reported. Efficient EROCM reactions of several oxa- and azabicycles, cyclobutenes and a cyclopropene proceed readily in the presence of 0.15�3 mol % of a stereogenic-at-Mo complex. The enantiomerically enriched disubstituted enol ethers are generated in high Z-selectivity. Functionalization of the enol ether can be easily differentiated from the terminal alkenes, which affords useful intermediates for chemical synthesis. In certain cases, enantioselectivity depends on cross partner concentration: larger equivalents of enol ethers generate the product with high enantioselectivity (versus near racemic products with one equivalent). Further mechanistic studies reveal that the length of reaction time can be critical to product enantiopurity: high selectivity obtained after 30 seconds can be nearly eroded within 30 minutes.

Efficient <i>Z</i>- and enantioselective ring-opening/cross-metathesis (ROCM) reactions promoted by stereogenic-at-Mo complexes

244th National Meeting (2012)

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Efficient Z- and enantioselective ring-opening/cross-metathesis (ROCM) reactions promoted by stereogenic-at-Mo complexes