Enolate conjugate addition to alkylidene bis-sulfoxides: Sphaeric acid synthesis and absolute configuration determination

The first stereoselective synthesis of sphaeric acid is described. The key step of this synthesis is an efficient ester enolate conjugate addition onto alkylidene bis-sulfoxides with good to high diastereoselectivity. Formation of sphaeric acid allowed the determination of its absolute configuration...

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Bibliographic Details
Published inSynlett no. 5; pp. 713 - 716
Main Authors Brebion, F, Goddard, JP, Gomez, C, Fensterbank, L, Malacria, M
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 17.03.2006
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
enolate addition
ACYCLIC STEREOSELECTION
E/Z-enolate
ASYMMETRIC-SYNTHESIS
sphaeric acid
STEREOCHEMISTRY
succinic acid
BIS(SULFOXIDES)
alkylidene bis-sulfoxides
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Summary:The first stereoselective synthesis of sphaeric acid is described. The key step of this synthesis is an efficient ester enolate conjugate addition onto alkylidene bis-sulfoxides with good to high diastereoselectivity. Formation of sphaeric acid allowed the determination of its absolute configuration as 2R,3R.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2006-933122