Facile, Asymmetric Addition of Acetylene to Aldehydes: In Situ Generation of Reactive Zinc Acetylide

This study documents a process in which acetylene is employed directly in nucleophilic additions to aldehydes to give adducts in high levels of enantiomeric induction, up to 98% ee. To the best of our knowledge, this represents the first time in which acetylene itself has been utilized in such ligan...

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Bibliographic Details
Published inHelvetica chimica acta Vol. 84; no. 4; pp. 964 - 971
Main Authors Sasaki, Hiroshi, Boyall, Dean, Carreira, Erick M.
Format Journal Article
LanguageEnglish
Published Basel Verlag Helvetica Chimica Acta 18.04.2001
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ALDOL ADDITIONS
ANALOGS
ALKYLATION
PROPARGYLIC ALCOHOLS
METHYL
1-ALKYNES
STEREOSPECIFIC SYNTHESIS
ENANTIOSELECTIVE ALKYNYLATION
DERIVATIVES
METATHESIS
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Summary:This study documents a process in which acetylene is employed directly in nucleophilic additions to aldehydes to give adducts in high levels of enantiomeric induction, up to 98% ee. To the best of our knowledge, this represents the first time in which acetylene itself has been utilized in such ligand‐controlled enantioselective additions.
Bibliography:ark:/67375/WNG-BHDHKL6S-H
ArticleID:HLCA964
istex:9056E871C4ACA2CD9502C86F235787E0A3C7A2B5
ISSN:0018-019X
1522-2675
DOI:10.1002/1522-2675(20010418)84:4<964::AID-HLCA964>3.0.CO;2-I