Enantioselective synthesis of α-alkenyl α-amino acids via N–H insertion reactions

A new highly enantioselective route to α-alkenyl α-amino acid derivatives using a N–H insertion reaction of vinyldiazoacetates and tert-butyl carbamate cooperatively catalyzed by achiral dirhodium(ii) carboxylates and chiral spiro phosphoric acids was developed.

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Enantioselective synthesis of β-amino acid derivatives via nickel-promoted regioselective carboxylation of ynamides and rhodium-catalyzed asymmetric hydrogenation

Organic & Biomolecular Chemistry ◽

10.1039/c6ob01234e ◽

2016 ◽

Vol 14 (42) ◽

pp. 10080-10089 ◽

Cited By ~ 22

Author(s):

Nozomi Saito ◽

Iman Abdullah ◽

Kayoko Hayashi ◽

Katsuyuki Hamada ◽

Momoko Koyama ◽

...

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Active Form ◽

Asymmetric Hydrogenation ◽

Optically Active ◽

Enantioselective Synthesis ◽

Amino Acid Derivatives

Nickel-promoted carboxylation of ynamides followed by rhodium-catalyzed asymmetric hydrogenation provided α-substituted-β-amino acids in an optically active form.

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Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.02,6]decane skeleton

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.5.81 ◽

2009 ◽

Vol 5 ◽

Cited By ~ 2

Author(s):

Matthias Breuning ◽

Tobias Häuser ◽

Christian Mehler ◽

Christian Däschlein ◽

Carsten Strohmann ◽

...

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Building Blocks ◽

Enantioselective Synthesis ◽

Side Chain ◽

Amino Acid Derivatives ◽

Chiral Auxiliaries ◽

Pyrrolidine Ring ◽

Asymmetric Organocatalysis

An enantioselective route to four tricyclic amino acids and N-tosylamides, composed of a central norbornane framework with a 2-endo,3-endo-annelated pyrrolidine ring and a 5-endo-C1 or -C2 side chain, has been developed. A key intermediate was the chiral, N-Boc-protected ketone (1R,2S,6S,7R)-4-azatricyclo[5.2.1.02,6]decan-8-one, available from inexpensive endo-carbic anhydride in five steps and 47% yield. The rigid scaffold makes these amino acid derivatives promising candidates for β-turn-inducing building blocks in peptidomimetics and for chiral auxiliaries in asymmetric organocatalysis.

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Enantioselective synthesis of cyclic quaternary α-amino acid derivatives by chiral phosphoric acid catalysis

Organic & Biomolecular Chemistry ◽

10.1039/c7ob01149k ◽

2017 ◽

Vol 15 (28) ◽

pp. 6033-6041 ◽

Cited By ~ 11

Author(s):

Lei Wang ◽

Abdul Rahman ◽

Xufeng Lin

Keyword(s):

Amino Acid ◽

Phosphoric Acid ◽

Acid Catalysis ◽

Enantioselective Synthesis ◽

Amino Acid Derivatives ◽

Chiral Phosphoric Acid ◽

Efficient Route ◽

Quaternary Stereocenter ◽

High Yields ◽

Phosphoric Acids

Development of highly enantioselective aza-Friedel–Crafts reaction of N-sulfonyl cyclic ketimines with indoles catalyzed by chiral phosphoric acids, providing an efficient route to indole-containing chiral cyclic α-amino acid derivatives bearing quaternary stereocenter in high yields and up to 98% enantioselectivity.

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An enantioselective synthesis of β2-amino acid derivatives

Tetrahedron Asymmetry ◽

10.1016/j.tetasy.2005.01.048 ◽

2005 ◽

Vol 16 (7) ◽

pp. 1309-1319 ◽

Cited By ~ 23

Author(s):

Jomana Elaridi ◽

Ali Thaqi ◽

Andrew Prosser ◽

W. Roy Jackson ◽

Andrea J. Robinson

Keyword(s):

Amino Acid ◽

Enantioselective Synthesis ◽

Amino Acid Derivatives

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ChemInform Abstract: Enantioselective Synthesis of β-Aryl-γ-amino Acid Derivatives via Cu-Catalyzed Asymmetric 1,4-Reductions of γ-Phthalimido-Substituted α,β-Unsaturated Carboxylic Acid Esters

ChemInform ◽

10.1002/chin.200850070 ◽

2008 ◽

Vol 39 (50) ◽

Author(s):

Jun Deng ◽

Xiang-Ping Hu ◽

Jia-Di Huang ◽

Sai-Bo Yu ◽

Dao-Yong Wang ◽

...

Keyword(s):

Amino Acid ◽

Carboxylic Acid ◽

Enantioselective Synthesis ◽

Amino Acid Derivatives ◽

Unsaturated Carboxylic Acid ◽

Acid Esters

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Enantioselective synthesis of optically active cis-β-thio-α-amino acid derivatives through an organocatalytic cascade thio-Michael/ring opening process

Chemical Communications ◽

10.1039/c2cc30799e ◽

2012 ◽

Vol 48 (39) ◽

pp. 4713 ◽

Cited By ~ 22

Author(s):

Zhi-Cong Geng ◽

Ning Li ◽

Jian Chen ◽

Xiao-Fei Huang ◽

Bin Wu ◽

...

Keyword(s):

Amino Acid ◽

Ring Opening ◽

Optically Active ◽

Enantioselective Synthesis ◽

Amino Acid Derivatives ◽

Opening Process

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ChemInform Abstract: Catalytic Asymmetric Synthesis of Functionalized α,α-Disubstituted α-Amino Acid Derivatives from Racemic Unprotected α-Amino Acids via in situ Generated Azlactones.

ChemInform ◽

10.1002/chin.201242200 ◽

2012 ◽

Vol 43 (42) ◽

pp. no-no

Author(s):

Manuel Weber ◽

Wolfgang Frey ◽

Rene Peters

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Asymmetric Synthesis ◽

Amino Acid Derivatives ◽

Catalytic Asymmetric Synthesis ◽

Catalytic Asymmetric

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Synthesis of New β-Amino Acids via 5-Oxazolidinones and the Arndt - Eistert Procedure

Australian Journal of Chemistry ◽

10.1071/ch05199 ◽

2005 ◽

Vol 58 (11) ◽

pp. 778 ◽

Cited By ~ 13

Author(s):

Andrew B. Hughes ◽

Brad E. Sleebs

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Reductive Cleavage ◽

High Yield ◽

Amino Acid Derivatives ◽

Peptide Therapeutics

N-Methyl β-amino acids are potentially useful amino acid derivatives for incorporation in lead peptide therapeutics. The syntheses of five such compounds are presented. Their synthesis via 6-oxazinanones was low yielding. Alternatively, reductive cleavage of a 5-oxazolidinone gave the N-methyl α-amino acid, which was then homologated via an Arndt–Eistert procedure in high yield to give the N-methyl β-amino acid.

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