S N 1‐Type Reactions in the Presence of Water: Indium(III)‐Promoted Highly Enantioselective Organocatalytic Propargylation of Aldehydes | Zendy

Sinisi Riccardo | Zendy; Vita Maria Victoria | Zendy; Gualandi Andrea | Zendy; Emer Enrico | Zendy; Cozzi Pier Giorgio | Zendy

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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.

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