DISPIROKETALS IN SYNTHESIS .10 - FURTHER REACTIONS OF DISPOKE PROTECTED LACTATE AND GLYCOLATE ENOLATES

alpha-Hydroxy acids have been reacted with bis-dihydropyrans to give dispiroketal adducts (1,8,13,16-tetraoxadispiro[5.0.5.4]-hexadecan-14-ones). The enolates derived from these compound undergo reaction with electrophiles with generally high levels of diastereoselectivity. Subsequent deprotection o...

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Bibliographic Details
Published inTetrahedron Vol. 50; no. 24; pp. 7157 - 7176
Main Authors BOONS, GJ, DOWNHAM, R, KIM, KS, LEY, SV, WOODS, M
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 13.06.1994
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:alpha-Hydroxy acids have been reacted with bis-dihydropyrans to give dispiroketal adducts (1,8,13,16-tetraoxadispiro[5.0.5.4]-hexadecan-14-ones). The enolates derived from these compound undergo reaction with electrophiles with generally high levels of diastereoselectivity. Subsequent deprotection of these compounds gives alpha-hydroxy esters of high enantiomeric excess.
ISSN:0040-4020
DOI:10.1016/S0040-4020(01)85241-8