Kinetic Resolution of Oxazinones: An Organocatalytic Approach to Enantiomerically Pure β‐Amino Acids

Berkessel, Albrecht; Cleemann, Felix; Mukherjee, Santanu

doi:10.1002/anie.200502003

Cited by 93 publications

(28 citation statements)

References 44 publications

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“…They later found a more effective thiourea derivative 4 d [35] and employed it in the kinetic resolution of oxazinones whereby b-amino acid derivatives were obtained with high enantioselectivity (Scheme 20). [36] Nagasawa et al designed a novel bifunctional catalyst having guanidine and thiourea functional groups 10, which effectively promoted the Henry reaction with aliphatic cyclic aldehydes and branched aldehydes in the presence of KI as an additive to afford b- nitroamines in 82-90 % ee. [37] They subsequently found that use of a-substituted aldehydes improved the enantioselectivity to 95-99 % ee (Scheme 21).…”

Section: Bifunctional Thiourea Catalystsmentioning

confidence: 99%

Recent Progress in Chiral Brønsted Acid Catalysis

Akiyama¹,

Itoh²,

Fuchibe³

2006

Adv Synth Catal

881

183

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Section: Bifunctional Thiourea Catalystsmentioning

confidence: 99%

Recent Progress in Chiral Brønsted Acid Catalysis

Akiyama¹,

Itoh²,

Fuchibe³

2006

Adv Synth Catal

881

183

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“…Palomo Another laboratory, also reported an organocatalytic approach to enantiomerically pure β-amino acids using this kind of catalysts to realize the kinetic resolution of oxazinones [130] (Scheme 1-67).…”

Section: Cinchona Alkaloids Catalyzed Asymmetric Reactionsmentioning

confidence: 94%

A new era for organic synthesis—highlights of the recent progress

Yikang

2007

Front. Chem. China

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The major progress in organic synthesis since 2005 is briefly surveyed in two parts. The first part deals with some of the most impressive advances in the synthetic methodology, which includes: (1) metal-mediated synthetic reactions, with an emphasis on the olefin metathesis and gold-mediated reactions; (2) free radical-based organic synthesis; (3) synthetic transformations performed in a "one-pot" manner involving either tandem reactions or multicomponent reactions; (4) asymmetric reactions catalyzed by metal and organo-catalysts. The major advances in total synthesis of some complex natural products with significant biological activities are presented in the second part, with detailed illustrations of ten selected molecules, including dragmacidin F, abyssomicin C, 11-acetoxy-4-deoxyasbestinin D, pentacycloanammoxic acid, UCS1025A, (−)-merrilactone A, nigellamine A 2 , (+)-saxitoxin, and Tamiflu (an artificially designed natural product-like molecule). An array of complicated structures of the natural products synthesized over the last two years is also listed to serve as a convenient lead to the original literature for the prospective interested readers.Keywords organic synthesis, metal-mediated synthetic reaction, free radical reaction, "in one pot" reaction, asymmetric reaction, total synthesis of natural products Organic reactions are of central importance to organic synthetic methodology and underlie all types of organic A new era for organic synthesis-highlights of the recent progress

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“…Similarly, Connon [34] used a cinchona-alkaloid-based organocatalyst 8 for stereoselective ring opening of azalactones (Scheme 6, c) following related studies by Berkessel. [35] Dynamic kinetic resolution of azalactones may be advantageous to the kinetic resolution of N-carboxy anhydrides in terms of the maximum possible yield (100 % vs. 50 %). However the starting material may be more economical to prepare for the N-carboxy anhydrides.…”

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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Kinetic Resolution of Oxazinones: An Organocatalytic Approach to Enantiomerically Pure β‐Amino Acids

Cited by 93 publications

References 44 publications

Recent Progress in Chiral Brønsted Acid Catalysis

Recent Progress in Chiral Brønsted Acid Catalysis

A new era for organic synthesis—highlights of the recent progress

Mimicking Nature to Make Unnatural Amino Acids and Chiral Diamines

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