Ueber einen neue Bildungsweise des Aethylamins;

Strecker, Adolph

doi:10.1002/jlac.18500750104

Cited by 163 publications

(222 citation statements)

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“…Recently, the ever-increasing demand for the non-proteinogenic α-amino acids in a variety of scientific disciplines has promoted the development of novel methods for the asymmetric syntheses of α-amino acids. [1] Together with the classic Strecker reaction, [2] one of the most important reactions for the production of α-amino nitriles Ϫ key intermediates for the synthesis of α-amino acids Ϫ is asymmetric cyanation of imines (Scheme 1). [3] Several procedures requiring the use of chiral auxiliaries have been reported to afford α-amino nitriles with high selectivity.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Strecker Reactions between Aldimines and Trimethylsilyl Cyanide Promoted by Chiral N,N′‐Dioxides

et al. 2003

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Axially chiral N,N′‐dioxide Lewis base promoters have been developed and have for the first time been applied to the asymmetric synthesis of α‐amino nitriles through cyanide addition to aldimines. The chiral 3,3′‐dimethyl‐2,2′‐biquinoline N,N′‐dioxide 2 exhibited high enantioselectivity for asymmetric Strecker reactions between N‐benzhydrylimines and trimethylsilyl cyanide. In the presence of 1 equiv. of chiral promoter 2, the cyanosilylation of aldimines afforded the corresponding α‐amino nitriles with ee values of up to 95%. Optically pure products (99% ee) were obtained simply by recrystallization in the cases of some of the products. Moreover, the promoter 2 could be recovered and reused at least four times without any loss of enantioselectivity and reactivity. A putative mechanism for the enantioselective Strecker reactions is also discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Section: Introductionmentioning

confidence: 99%

Enantioselective Strecker Reactions between Aldimines and Trimethylsilyl Cyanide Promoted by Chiral N,N′‐Dioxides

et al. 2003

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“…Historically, alpha amino nitriles is the oldest multicomponent reaction reported by Streacker, which employs aldehydes, amines, and sodium cyanide/ potassium cyanide to afford a-amino nitriles (72 …”

Section: Streacker Reactionmentioning

confidence: 99%

Recent advances in ionic liquids: green unconventional solvents of this century: part II

Sandhu

2011

Green Chemistry Letters and Reviews

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“…A unique and efficient catalytic asymmetric total synthesis of epothilones A and B was achieved by combining three original catalytic asymmetric reactions developed in our laboratory, clearly demonstrating the practicality and power of these catalysts for the synthesis of complex molecules. 38) The catalytic asymmetric Strecker-type reaction 39) is one of the most direct and efficient methods for the asymmetric synthesis of natural and unnatural a-amino acids. Several excellent reactions of this type were recently reported.…”

Section: -2 Application To a Catalytic Asymmetric Total Synthesis Omentioning

confidence: 99%

Multifunctional Asymmetric Catalysis.

Shibasaki

Kanai

2001

Chem. Pharm. Bull.

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Two types of general and practical enantioselective catalysts, namely, bimetallic complexes and Lewis acid-Lewis base bifunctional catalysts were developed based on the concept of multifunctional catalysis. In the first part of this review, the first example of a catalytic enatioselective nitro-Mannich reaction as well as a direct catalytic enantioselective aldol reaction of 2-hydroxyacetophenone using bimetallic complexes is discussed. The new complex, composed of ytterbium, potassium, and BINOL in a ratio of 1 : 1 : 3, promoted the nitro-Mannich reaction of nitromethane with up to 91% ee. On the other hand, second generation ALB catalyzed an enantioselective and diastereoselective nitro-Mannich reaction of nitroalkanes in up to 83% ee with a diastereomeric ratio up to 7 : 1. Moreover, the reaction of aldehydes with 2-hydroxyacetophenone in the presence of LLB, KHMDS, and H 2 O selectively gave the corresponding anti-a a,b b-dihydroxy ketones in up to 95% ee and, in the presence of the catalyst prepared from linked-BINOL and 2 eq of Et 2 Zn, selectively afforded the syn-a a,b b-dihydroxy ketones in up to 86% ee. In the second part, the development of new catalysts displaying a Lewis acidity and a Lewis basicity is described. The Lewis acid of the catalyst activates aldehydes, imines, acyl quinoliniums, and ketones. At the same time, the Lewis base activates the nucleophile (TMSCN). Catalysts of this type produced a highly enantioselective cyanation of these electrophiles. Application of the catalytic enantioselective cyanosilylation of aldehydes to a total synthesis of epothilones is also described.

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Ueber einen neue Bildungsweise des Aethylamins;

Cited by 163 publications

References 0 publications

Enantioselective Strecker Reactions between Aldimines and Trimethylsilyl Cyanide Promoted by Chiral N,N′‐Dioxides

Enantioselective Strecker Reactions between Aldimines and Trimethylsilyl Cyanide Promoted by Chiral N,N′‐Dioxides

Recent advances in ionic liquids: green unconventional solvents of this century: part II

Multifunctional Asymmetric Catalysis.

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