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Synlett 2014; 25(6): 783-794
DOI: 10.1055/s-0033-1340618
DOI: 10.1055/s-0033-1340618
account
The Anion-Binding Approach to Catalytic Enantioselective Acyl Transfer
Further Information
Publication History
Received: 14 November 2013
Accepted: 03 December 2013
Publication Date:
27 January 2014 (online)
Abstract
This account details the development of a dual-catalysis approach and its application to the kinetic resolution of amines and other enantioselective acyl-transfer reactions. Anion recognition is an essential design element of these processes, which are enabled by the combined action of an achiral 4-(N,N-dimethylamino)pyridine (DMAP) derivative and a chiral anion receptor catalyst.
1 Introduction
2 Kinetic Resolution of Amines
2.1 Benzylic Amines
2.2 Propargylic Amines
2.3 Allylic Amines
2.4 Benzylic Amines Revisited
2.5 Racemic Diamines
3 Desymmetrization of meso-Diamines
4 Miscellaneous Acyl Transfer Reactions
4.1 Steglich Reaction
4.2 Reactions of Isoquinolines with Azlactones
4.3 Acylation of Silyl Ketene Acetals
5 Conclusions
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For selected reviews on anion receptor chemistry, see:
For selected reviews on chiral anion catalysis, see:
For other examples of catalytic processes that likely involve anion binding, see:
For selected reviews covering various aspects of asymmetric nucleophilic catalysis, acyl-transfer, and kinetic resolution, see:
For selected reviews on hydrogen-bonding catalysis, see:
For selected reviews on cooperative catalysis, see:
For selected reviews on enzymatic amine acylation, see:
See also:
For selected examples of amine resolution with chiral acylating reagents, see:
For other selected catalytic approaches to the kinetic resolution of amines, see:
For selected reports on the formation, nature, and reactivity of acylpyridinium salts, see:
For selected reviews on DMAP catalysis, see:
Self-aggregation of organocatalysts can have a dramatic impact on enantioselectivities. For examples, see:
For reports on the reactivity of these nucleophilic catalysts, see:
For selected reviews on azlactone rearrangements and related reactions, see: