Unusual Reversal of Enantioselectivity in the Proline-Mediated α-Amination of Aldehydes Induced by Tertiary Amine Additives | Zendy

Donna G. Blackmond | Zendy; Antonio Morán | Zendy; Matthew Hughes | Zendy; Alan Armstrong | Zendy

Open Access

Unusual Reversal of Enantioselectivity in the Proline-Mediated α-Amination of Aldehydes Induced by Tertiary Amine Additives

Author(s) -

Donna G. Blackmond,

Antonio Morán,

Matthew Hughes,

Alan Armstrong

Publication year - 2010

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja102718x

Subject(s) - chemistry , tertiary amine , amine gas treating , proline , amination , organic chemistry , medicinal chemistry , amino acid , biochemistry , catalysis

An intriguing reversal in product enantioselectivity accompanied by a change in the kinetic profile is observed in the alpha-amination of aldehydes catalyzed by proline in the presence of organic bases. Implications for the prevailing stereochemical models for proline and related aminocatalytic transformations are discussed.

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