Asymmetric Ir(I-)catalysed allylic alkylation of monosubstituted allylic acetates with phosphorus amidites as ligands

Monodentate phosphorus amidites derived from 2,2'-binaphthol and a variety of chiral amines were employed as ligands in Ir-I -catalysed allylic alkylations of unsymmetrically substituted allylic acetates. The enantio- and regioselectivities of these reactions were investigated. Phosphorus amidi...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2003; no. 6; pp. 1097 - 1103
Main Authors Bartels, B, Garcia-Yebra, C, Helmchen, G
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.03.2003
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SUBSTITUTION
1,10-PHENANTHROLINE LIGANDS
chirality
REACTIVITY
asymmetric catalysis
REGIOCONTROL
iridium
AMINATION
STEREOSELECTIVITY
ENONES
P ligands
DIALKYLZINC REAGENTS
allylic substitution
CATALYTIC CONJUGATE ADDITION
IRIDIUM COMPLEX
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Summary:Monodentate phosphorus amidites derived from 2,2'-binaphthol and a variety of chiral amines were employed as ligands in Ir-I -catalysed allylic alkylations of unsymmetrically substituted allylic acetates. The enantio- and regioselectivities of these reactions were investigated. Phosphorus amidites of bulky secondary chiral amines induced enantioselectivities of up to 94% ee in reactions of linear substrates. Phosphorus amidites derived from chiral primary amines, which have not been previously employed in asymmetric catalysis, furnished improved regioselectivities, The use of LiCl as additive led to improved regio- and enantioselectivities.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200390162