A catalytic and enantioselective cyclopropylation of aldehydes using dicyclopropylzinc

Enantioselective cyclopropylation of various aldehydes proceeds using dicyclopropylzine in the presence of a catalytic amount of chiral amino alcohol or thiophosphoramidate with Ti(OPri)(4) to provide enantiomerically enriched cyclopropyl alkanols (up to 96.6% ee).

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Bibliographic Details
Published inJournal of the Chemical Society, Perkin Transactions 1 no. 2; pp. 177 - 178
Main Authors Shibata, T, Tabira, H, Soai, K
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1998
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANOZINC REAGENTS
SECONDARY ALCOHOLS
CHIRAL CATALYST
ORGANIC-SYNTHESIS
HIGHLY DIASTEREOSELECTIVE REDUCTION
ALPHA-AMINO KETONE
ASYMMETRIC-SYNTHESIS
STEREOSPECIFIC ARYLATION
DIALKYLZINC REAGENTS
CARBONYL-COMPOUNDS
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Summary:Enantioselective cyclopropylation of various aldehydes proceeds using dicyclopropylzine in the presence of a catalytic amount of chiral amino alcohol or thiophosphoramidate with Ti(OPri)(4) to provide enantiomerically enriched cyclopropyl alkanols (up to 96.6% ee).
ISSN:0300-922X
1364-5463
DOI:10.1039/a707315a