SN1-Type Reactions in the Presence of Water: Indium(III)-Promoted Highly Enantioselective Organocatalytic Propargylation of Aldehydes

Water under troubled chemistry! The first catalytic stereoselective addition of aldehydes to internal functionalized propargylic alcohols promoted by a combination of organocatalysis and indium triflate is described (see scheme). The reaction is tolerant of functional groups (FG) and was performed i...

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Published inChemistry : a European journal Vol. 17; no. 27; pp. 7404 - 7408
Main Authors Sinisi, Riccardo, Vita, Maria Victoria, Gualandi, Andrea, Emer, Enrico, Cozzi, Pier Giorgio
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 27.06.2011
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
Subjects
aldehydes
Chemistry
enamine
indium
organocatalysis
propargylation
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Summary:Water under troubled chemistry! The first catalytic stereoselective addition of aldehydes to internal functionalized propargylic alcohols promoted by a combination of organocatalysis and indium triflate is described (see scheme). The reaction is tolerant of functional groups (FG) and was performed in the presence of water. High enantioselectivities (anti, 92–99 % ee) and moderate diastereomeric ratios (d.r., up to 6.7:1 for the anti isomer) were obtained.
Bibliography:PRIN
istex:0C8D604C727C5A340BC00987E7876F004FA6BAED
ark:/67375/WNG-2G8TDJKN-K
Progetto Nazionale Stereoselezioni in Chimica Organica: Metodologie ed Applicazioni
European Commission - No. FP7-201431
Fondazione Del Monte
Bologna University
ArticleID:CHEM201100729
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201100729