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S N 1‐Type Reactions in the Presence of Water: Indium(III)‐Promoted Highly Enantioselective Organocatalytic Propargylation of Aldehydes
Author(s) -
Sinisi Riccardo,
Vita Maria Victoria,
Gualandi Andrea,
Emer Enrico,
Cozzi Pier Giorgio
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201100729
Subject(s) - enantioselective synthesis , diastereomer , organocatalysis , indium , chemistry , stereoselectivity , catalysis , trifluoromethanesulfonate , organic chemistry , medicinal chemistry
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.