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Enantioselective synthesis of cyclic allylboronates by Mo-catalyzed asymmetric ring-closing metathesis (ARCM). A one-pot protocol for net catalytic enantioselective cross metathesis
Authors:Jesper A Jernelius  Amir H Hoveyda
Institution:a Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467, USA
b Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02138, USA
Abstract:Mo-catalyzed asymmetric ring-closing metathesis (ARCM) reactions are used to synthesize cyclic allylboronates of high optical purity (89% ee to >98% ee). A one-pot procedure involving formation of allylboronates, Mo-catalyzed ARCM and functionalization of the optically enriched cyclic allylboronates constitutes net asymmetric cross metathesis (ACM). Structural modification of ARCM products include reactions with aldehydes to afford optically enriched compounds that bear quaternary carbon centers with excellent diastereoselectivity. These studies emphasize the significance of the availability of chiral Mo-based complex as a class of chiral metathesis catalysts that frequently complement one another in terms of reactivity and selectivity.
Keywords:Allylboronates  Asymmetric cross metathesis  Asymmetric ring-closing metathesis
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