Hydrogen-bonding asymmetric metal catalysis with α-amino acids: A simple and tunable approach to high enantioinduction

Journal of the American Chemical Society

Volumn 131, Issue 32, 2009, Pages 11284-11285

  Lu, Yingdong ^a   Johnstone, Tim C ^a   Arndtsen, Bruce A ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYLATIONS; AMINO ACID DERIVATIVES; CHEMICAL EQUATIONS; CHIRAL CATALYST; CHIRAL ENVIRONMENT; CHIRAL PRODUCT; COPPER CATALYST; HIGH ENANTIOSELECTIVITY; HIGH SELECTIVITY; HYDROGEN BONDINGS; METAL CATALYSIS; RAPID SCREENING; SIMPLE APPROACH; TUNABLE LIGANDS;

AMINATION; AMINES; AMINO ACIDS; CATALYSTS; ENANTIOSELECTIVITY; HYDROGEN; LIGANDS; ORGANIC ACIDS; TRANSITION METALS;

CATALYSIS;

ALPHA AMINO ACID; AMINO ACID DERIVATIVE; BRONSTED ACID; COPPER; LIGAND; MOLECULAR SCAFFOLD;

ALKYNYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL PROCEDURES; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; HYDROGEN BOND; SCREENING;

AMINO ACIDS; CATALYSIS; HYDROGEN BONDING; IMINES; METALS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 68849089005     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja904185b     Document Type: Article

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32. 6], also suggesting separate roles for Cu and the amino acid in the reaction (see the Supporting Information). Notably, other H-bonding acids can also lead to enantioselectivity, though at lower ee's [(S)-mandelic acid, 19% ee; L-2-pyrrolidone-5-carboxylic acid, 0% ee].
33. See the Supporting Information for configuration assignment (for 2b and 2g, see ref 9c).