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Enantioselective Protonation Catalyzed by a Chiral Bicyclic Guanidine Derivative

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This article is published in Angewandte Chemie.The article was published on 2008-07-14. It has received 161 citations till now. The article focuses on the topics: Bicyclic molecule & Protonation.

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Bicyclic-guanidines, -guanidinates and -guanidinium salts: wide ranging applications from a simple family of molecules

TL;DR: The chemistry of bicyclic guanidinate anions is reviewed in light of recent advances in the synthesis of new derivatives, highlighting the potential for cross-stimulation of different areas.
Journal ArticleDOI

Chiral guanidine catalyzed enantioselective reactions.

TL;DR: This article highlights the development of chiral guanidine catalysis in asymmetric synthesis with high catalytic activities and enantioselectivities.
Journal ArticleDOI

Enantioselective Synthesis of Chiral Allenoates by Guanidine-Catalyzed Isomerization of 3-Alkynoates

TL;DR: It is reported that chiral bicyclic guanidine 1 is found to catalyze the isomerization of alkynes to chiral allenes with high enantioselectivities and the axial chirality of the allenes is efficiently transferred to functionalized butenolides and cycloaddition products.
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The chemistry and biology of organic guanidine derivatives

TL;DR: The literature survey includes purely synthetic Guanidine derivatives, guanidine alkaloids and non-ribosomal peptides from bacteria and cyanobacteria, as well as related compounds isolated from marine and terrestrial invertebrates and higher plants.
References
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Journal ArticleDOI

Enantioselective Synthesis of α-Amino Nitriles from N-Benzhydryl Imines and HCN with a Chiral Bicyclic Guanidine as Catalyst

TL;DR: A novel catalytic enantioselective Strecker synthesis of chiral alpha-amino nitriles and alpha-AMino acids is described and analyzed with regard to the possible mechanistic basis for stereoselectivity.
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Asymmetric multicomponent domino reactions and highly enantioselective conjugated addition of thiols to alpha,beta-unsaturated aldehydes.

TL;DR: An organocatalytic asymmetric multicomponent domino and a conjugated addition reaction to α,β-unsaturated aldehydes are presented, which give enantiopure amino−thiols in moderate to good yields and excellent enantioselectivities.
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Control of Diastereoselectivity in Tandem Asymmetric Reactions Generating Nonadjacent Stereocenters with Bifunctional Catalysis by Cinchona Alkaloids

TL;DR: This manipulation of hydrogen-bonding-based cooperative catalysis to control the diastereoselectivity for a tandem asymmetric reaction creating two nonadjacent stereocenters allows, for the first time, the direct and stereoselective construction of 1,3-tertiary−quaternary stereocenter in any of the possible four configurations from the same prochiral precursors with catalytic control.
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Asymmetric Catalysis of the Strecker Amino Acid Synthesis by a Cyclic Dipeptide

TL;DR: In this paper, a cyclic dipeptide called cyclo[(S)-His-(S)-NorArg] has been prepared which catalyzes an enantioselective version of the Strecker amino acid synthesis.
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Dual-function cinchona alkaloid catalysis: catalytic asymmetric tandem conjugate addition-protonation for the direct creation of nonadjacent stereocenters.

TL;DR: This is the first asymmetric tandem conjugate addition-protonation with efficient catalytic control of two nonadjacent stereocenters and establishes a new and versatile catalytic approach for the enantioselective and diastereoselectives creation of 1,3-tertiary-quaternary stereocenter.
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