Organocatalytic Asymmetric Biomimetic Transamination: From α-Keto Esters to Optically Active α-Amino Acid Derivatives

Xiao, Xiao; Xie, Ying; Su, Cunxiang; Liu, Mao; Shi, Yian

doi:10.1021/ja203138q

Cited by 130 publications

(47 citation statements)

References 81 publications

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“…34 Various chiral bases were examined with ethyl 2-oxo-4-phenylbutanoate (36) as the substrate and o-ClPhCH 2 NH 2 (37) as the nitrogen source (Scheme 13). Up to 69% ee was obtained with quinine derived .…”

Section: Catalytic Asymmetric Transaminationmentioning

confidence: 99%

Progress in asymmetric biomimetic transamination of carbonyl compounds

et al. 2015

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Transamination of α-keto acids with transaminases and pyridoxamine phosphate is an important process to form optically active α-amino acids in biological systems. Various biomimetic transamination systems have been developed for carbonyl compounds including α-keto acid derivatives, fluoroalkyl ketones, and unactivated ketones with chiral vitamin B6 analogues, artificial transaminase mimics, chiral nitrogen sources, and chiral catalysts. This review provides a brief summary of this area.

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Section: Catalytic Asymmetric Transaminationmentioning

confidence: 99%

Progress in asymmetric biomimetic transamination of carbonyl compounds

et al. 2015

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“…Very recently, Shi [47] reported a highly stereoselective transamination reaction (up to 92 %ee) for making α-amino acids in excellent yield (100 %) using cinchona alkaloid as a general base catalyst (10 mol-%). Stereoselective catalytic reduction [48] or alkylation [49] of α-keto ester imines are also efficient routes to amino acids.…”

Section: Stereoselective Catalysts For the Synthesis Of α-Amino Acidsmentioning

confidence: 99%

Mimicking Nature to Make Unnatural Amino Acids and Chiral Diamines

So¹,

Kim

Mui

et al. 2011

Eur J Org Chem

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Keywords: Amino acids / Amines / Transamination / Rearrangement / Chiral resolution Biomimetic studies of pyridoxal and pyridoxamine models are of both fundamental and practical interest. This review examines (i) deracemization of α-amino acids with a chiral pyridoxal model, (ii) sensing of chirality of small molecules including α-, β-, and γ-amino acids, peptides, amino alcohols and diamines with an achiral pyridoxal model and (iii) stereospecific synthesis of chiral diamines with a chiral pyridoxamine model. A binol-based aldehyde is useful as a chiral pyridoxal model to deracemize a variety of α-amino acids to make D-amino acids. 2,2Ј-Dihydroxybenzophenone is useful

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“…In contrast, umpolung of trifluoromethyl imines, that is, inverting the polarization of imines as a nucleophile, may provide alternative access to structures and addition patterns which are not (or hardly) accessible by previous methods (Scheme 1 a, right-hand side). [4,5] However, this strategy poses considerable challenges because of the unavoidable reversal of the inherent electrophilicity of imines. Only one example of Figure 1.…”

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Phosphine‐Catalyzed Asymmetric Umpolung Addition of Trifluoromethyl Ketimines to Morita–Baylis–Hillman Carbonates

et al. 2016

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A novel phosphine-catalyzed, highly enantioselective umpolung addition of trifluoromethyl ketimines to Morita-Baylis-Hillman carbonates was developed and it provides facile access to optically active trifluoromethyl amines with a chiral tertiary stereocenter under mild reaction conditions. The salient features of this reaction include general substrate scope, mild reaction conditions, good yields, high enantioselectivity, ease of scale-up to gram scale, and further transformations of the products.

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Organocatalytic Asymmetric Biomimetic Transamination: From α-Keto Esters to Optically Active α-Amino Acid Derivatives

Abstract: This paper describes an effective chiral base-catalyzed biomimetic transamination of α-keto esters using simple benzyl amines. A wide variety of α-amino esters containing various functional groups can be synthesized in high enantioselectivity and reasonable yield.

Cited by 130 publications

References 81 publications

Progress in asymmetric biomimetic transamination of carbonyl compounds

Progress in asymmetric biomimetic transamination of carbonyl compounds

Mimicking Nature to Make Unnatural Amino Acids and Chiral Diamines

Phosphine‐Catalyzed Asymmetric Umpolung Addition of Trifluoromethyl Ketimines to Morita–Baylis–Hillman Carbonates

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