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Glycolate aldol reactions with boron enolates of bis-4-methoxyphenyl dioxanone

✍ 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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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

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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