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A stereoselective aldol reaction via diisopinocampheyl boron-enolate in preparation of chromane carboxylate with quaternary carbon |
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| Authors: | Fengrui Lang Daniel ZewgeMirlinda Biba Peter DormerDavid Tschaen RP VolantePaul J Reider |
| Institution: | a Department of Process Research, Merck Research Laboratories, WYN-3, 466 Devon Park Drive, Wayne, PA 19087, USA b Department of Process Research, Merck Research Laboratories, PO Box 2000, Rahway, NJ 07065, USA |
| Abstract: | A highly stereoselective aldol reaction was observed on chromane carboxylate ester 1 via the corresponding diisopinocampheyl boron-enolate using commercially available (−)-DIP-Cl reagent. The aldol product 2c was obtained in 89% yield with 48 dr and 92% ee. Further studies indicate that stereoselective formation of the enolate and proper chiral ligand on boron are responsible for the exceptional diastereo- and enantioselectivity in the aldol reaction. |
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