Catalytic Enantioselective Addition of Diorganozinc Reagents to Vinyl Sulfones
نویسندگان
چکیده
منابع مشابه
Catalytic asymmetric addition of diorganozinc reagents to N-phosphinoylalkylimines.
The synthesis of alpha-chiral amines bearing two alkyl groups has been hampered by the accessibility and stability of the alkylimine precursor. Herein, we report an efficient strategy to generate the alkyl-substituted imine in situ that is compatible with the Me-DuPHOS monoxide.Cu(I) catalyzed addition of diorganozinc reagents. The sulfinic acid adduct of the imine is readily prepared by mixing...
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Chiral framework: Chiral amines with pyrrolidine frameworks catalyze the enantioselective conjugate addition of a wide range of aldehydes to various vinyl sulfones and vinyl phosphonates in high yields and with enantioselectivities up to >99 % ee (see scheme). The high versatility of the Michael adducts is exemplified by various functionalizations with conservation of the optical purity.Chiral ...
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α-Chiral amines are of significant importance in medicinal chemistry, asymmetric synthesis and material science, but methods for their efficient synthesis are scarce. In particular, the synthesis of α-chiral amines with the challenging tetrasubstituted carbon stereocentre is a long-standing problem and catalytic asymmetric additions of organometallic reagents to ketimines that would give direct...
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The copper-catalyzed diorganozinc addition to N-diphenylphosphinoylimines was shown to proceed with a very high degree of enantiocontrol if the reaction was run in the presence of Me-DuPHOS monoxide ligand (BozPHOS). The scope of the reaction is described as well as our efforts to identify the nature of the enantioactive metal complex responsible for the high asymmetric induction.
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The addition of Grignard reagents to aldehydes in the presence of chiral aminoalcohols shows a moderate enantioselectivity. The study carried out with a series of ligands allows the correlation between the structural characteristics and their reactivity. Introduction The use of chiral aminoalcohol to lead asymmetrically nucleophilic additions of organometallics to carbonyl compounds is a field ...
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2008
ISSN: 1523-7060,1523-7052
DOI: 10.1021/ol802157q