Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 5, Issue 3, Pages 562-570Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.200900344
Keywords
alkylation; asymmetric synthesis; diastereoselectivity; hydroxylation; phase-transfer catalysis
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan
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Highly enantioselective phase-transfer-catalyzed alkylation of tert-butyl 2-benzoyloxy-3-oxobutanoate was realized by the use of an N-spiro chiral quaternary ammonium salt, as a complementary approach to the asymmetric hydroxylation of alpha-alkyl-beta-keto esters. The synthetic utility of the alkylated compounds is highlighted by the diastereoselective reduction and alkylation of the remaining ketone moiety to give various enantiomerically enriched congested 2,3-dihydroxy-carboxylic acid esters.
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