Glycolate aldol reactions with boron enolates of bis-4-methoxyphenyl dioxanone
β Scribed by Merritt B Andrus; Kris G Mendenhall; Erik L Meredith; B.B.V Soma Sekhar
- Book ID
- 104250577
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 132 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
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 stereoselect
Boron enolates bearing menthone-derived chiral ligands are capable of fair to excellent diastereocontrol in their reactions with chiral aldehydes. Thioester-derived (better than ketone derived) enolates are able to control aldol stereochemistry irrespective of the aldehyde preferences. With thioacet