Catalytic, Enantioselective Synthesis ofα-Aminonitriles with a Novel Zirconium Catalyst

Ishitani, Haruro; Komiyama, Susumu; Kobayashi, Shū

doi:10.1002/(sici)1521-3773(19981204)37:22<3186::aid-anie3186>3.0.co;2-e

Cited by 157 publications

(37 citation statements)

References 6 publications

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“…66 Typically, the catalytic asymmetric Strecker reaction with metal complexes show high catalytic capability and could be achieved with very low catalyst loading and higher enantioselectivities. Chiral metal complexes represent an interesting and important group of catalysts for the catalytic enantioselective addition of cyanide donors to imines.…”

Section: Scheme 33mentioning

confidence: 99%

Recent advances on asymmetric Strecker reactions

Cai¹,

Xie²

2014

Arkivoc

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The Strecker reaction is one of the most attractive methods for the synthesis of α-amino acids and other bioactive compounds including natural products. The asymmetric Strecker reaction represents a simple and efficient method for the synthesis of optically pure α-amino acid derivatives, nucleic acids, various nitrogen and sulfur containing heterocycles and pharmaceuticals. Over the past several decades, considerable effort has been devoted towards the development of asymmetric Strecker reactions. This review provides an overview of recent asymmetric Strecker reactions, from diastereoselective reactions and catalytic enantioselective reactions including chiral catalytic metal systems and chiral organocatalytic systems.

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Section: Scheme 33mentioning

confidence: 99%

Recent advances on asymmetric Strecker reactions

Cai¹,

Xie²

2014

Arkivoc

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“…Aminonitrile-containing scaffolds are of significant interest in organic chemistry , and are usually prepared by the nucleophilic addition of cyanide to an imine; also known as the Strecker reaction. − This reaction is an important process in organic synthesis and provides access to a wide range of key precursors that act as building blocks in the pharmaceutical industry. − Standard catalytic processes using homogeneous catalysts are efficient; − however, they require expensive or toxic catalytic systems . The use of these catalysts presents difficulties in separation, scalability, tedious workup, and waste production .…”

Section: Introductionmentioning

confidence: 99%

Rutile Promoted Synthesis of Sulfonylamidonitriles from Simple Aldehydes and Sulfonamides

Costantini

Bates

Haun

et al. 2016

ACS Sustainable Chem. Eng.

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We report the first rutile-promoted synthesis of sulfonylamidonitriles from aldehydes and sulfonamides with NaCN in water. This transformation has proven to work for a variety of aliphatic and aromatic aldehydes with excellent yields. The scope also extends to a variety of substituted sulfonamides. Rutile can be easily recycled and reused without significant reaction erosion. The benign nature of rutile and its natural abundance highlights this transformation as a model green reaction.

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“…In the literature, only a few examples are reported showing the use of mixtures of chiral catalysts, varying either in the metal ion or in the chiral ligand. [3][4][5][6][7][8][9][10] In general, the catalytic species or the chiral ligands in these cases do have a different role. In our study we clearly intended to test a mixture of catalysts with the same catalytic function.…”

Section: Introductionmentioning

confidence: 99%