Journal ArticleDOI
Dual Lewis Acid−Lewis Base Activation in Enantioselective Cyanation of Aldehydes Using Acetyl Cyanide and Cyanoformate as Cyanide Sources
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TLDR
C cyanation of both aromatic and aliphatic aldehydes with acetyl cyanide and ethyl cyanoformate to provide direct access to O-acetylated and O-alkoxycarbonylated cyanohydrins, respectively, under mild conditions.Abstract:
Dual activation by a chiral Lewis acid and an achiral or chiral Lewis base enabled cyanation of both aromatic and aliphatic aldehydes with acetyl cyanide and ethyl cyanoformate to provide direct access to O-acetylated and O-alkoxycarbonylated cyanohydrins, respectively, under mild conditions. With a combination of a Ti−salen catalyst and Et3N, benzaldehyde was converted to the O-acetylated cyanohydrin with 94% ee within 10 h at −40 °C in 89% isolated yield.read more
Citations
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Catalytic Enantioselective Formation of C−C Bonds by Addition to Imines and Hydrazones: A Ten-Year Update
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Bifunctional Asymmetric Catalysis: Cooperative Lewis Acid/Base Systems
TL;DR: Three separate bifunctional methods that combine achiral Lewis acids with chiral cinchona alkaloid nucleophiles, for example, benzoylquinine (BQ), to catalyze highly enantioselective cycloaddition reactions between ketene enolates and various electrophiles are contributed.
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Lewis acid catalyzed asymmetric cyanohydrin synthesis.
TL;DR: This paper presents a meta-analyses of C1-Symmetric Schiff Bases for the Asymmetric Cyanation of Ketones using Boron-Based Catalytic Systems and concludes that these systems are likely to be incompatible with each other.
Journal ArticleDOI
Asymmetric carbon-carbon bond formation under continuous-flow conditions with chiral heterogeneous catalysts.
TL;DR: The recent progress in asymmetric C-C bond-forming reactions under continuous-flow conditions with chiral heterogeneous catalysts is summarized.
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Catalytic Asymmetric Cyanation Reactions
Nobuhito Kurono,Takeshi Ohkuma +1 more
TL;DR: A review of catalytic asymmetric conjugate cyanidation of prochiral unsaturated compounds can be found in this paper, with a focus on the use of chiral metal complexes and organocatalysts.
References
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Journal ArticleDOI
Synthesis and applications of non-racemic cyanohydrins
TL;DR: In this paper, a review of catalytic asymmetric synthesis of cyanohydrins derived from both aldehydes and ketones is presented, and several successful catalysts based on enzymes, peptides and transitional metal complexes are described.
Journal ArticleDOI
Synthesis and Reactions of Optically Active Cyanohydrins
TL;DR: A review of chiral cyanohydrins can be found in this paper, where the authors discuss enantioselective addition of hydrogen cyanide (HCN), catalysed by the enzymes (R)-and (S)-oxynitrilase, to aldehydes and Ketones yielding (R) and (S) cyanohydrin, respectivity.
Journal ArticleDOI
The Asymmetric Addition of Trimethylsilyl Cyanide to Aldehydes Catalyzed by Chiral (Salen)Titanium Complexes
Yuri N. Belokon,† Susana Caveda-Cepas,Brendan Green,Nicolai S. Ikonnikov,Viktor N. Khrustalev,Vladimir S. Larichev,Margarita A. Moscalenko,Michael North,Charles Orizu,Vitali I. Tararov,Michela Tasinazzo,and Galina I. Timofeeva,Lidia V. Yashkina +12 more
TL;DR: The use of chiral (salen)TiCl2 complexes to induce the asymmetric addition of trimethylsilyl cyanide to aldehydes has been investigated in this paper.
Journal ArticleDOI
Linked-BINOL: An Approach towards Practical Asymmetric Multifunctional Catalysis
TL;DR: The development and application of a novel linked-1,1′-binaphthol (linked-BINOL) as an approach towards practical asymmetric multifunctional catalysis is described.
Journal ArticleDOI
Catalytic Asymmetric Synthesis of O‐Acetylcyanohydrins from Potassium Cyanide, Acetic Anhydride, and Aldehydes, Promoted by Chiral Salen Complexes of Titanium(IV) and Vanadium(V)
Yuri N. Belokon,Paola Carta,Andrey V. Gutnov,Viktor Maleev,M. A. Moskalenko,L. V. Yashkina,Nicolai S. Ikonnikov,Nikolai V. Voskoboev,V. N. Khrustalev,Michael North +9 more
TL;DR: In this paper, the utility of the chiral [Ti(μ-O)(salen)]2 complexes (R)- and (S)-1 (H2salen) for asymmetric addition of KCN and Ac2O to aldehydes to produce O-acetylcyanohydrins was investigated.
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