✦ LIBER ✦
A stereoselective aldol reaction via diisopinocampheyl boron-enolate in preparation of chromane carboxylate with quaternary carbon
✍ Scribed by Fengrui Lang; Daniel Zewge; Zhiguo J Song; Mirlinda Biba; Peter Dormer; David Tschaen; R.P Volante; Paul J Reider
- Book ID
- 104253893
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 121 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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.