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Stereoselective aldol condensation. Use of chiral boron enolates

✍ Scribed by Masamune, Satoru; Choy, William; Kerdesky Francis A. J., ; Imperiali, Barbara

Book ID: 120057865
Publisher: American Chemical Society
Year: 1981
Tongue: English
Weight: 360 KB
Volume: 103
Category: Article
ISSN: 0002-7863
DOI: 10.1021/ja00396a050

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A study on the addition of boron enolates of methyl ketones to trans a,b-epoxy aldehydes is reported. The reaction proceeds with an excellent anti stereoselectivity, consistent with the Felkin-Ahn model, toward the synthesis of hydroxylated compounds with defined stereochemistry.

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## Abstract For Abstract see ChemInform Abstract in Full Text.

Enantioselective aldol condensations: Th

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Aldol condensation between diethylketone and simple aldehydes using (lpc)2BOTfliPr2NEt in CH,CI, gives syn-adducts in good ee (66-90%) and with high diastereoselectivity (290%). Other chiral dialkylboron triflate reagents examined give lower ees. The aldol condensation reaction of boron enolates, l