ChemInform Abstract: Nucleophilic Ring Opening of Aryl α-Nitrocyclopropane Carboxylates with Sterically Protected but Electronically Effective Carbonyl and Nitro Group. A New Principle of α-Amino Acid Synthesis (2-Aminobutanoic Acid a4-Synthon).

Ring-opening of N-(PhF)serine-derived cyclic sulfamidate 17 was achieved with different nucleophiles (β-keto esters, β-keto ketones, dimethyl malonate, nitroethane, sodium azide, imidazole, and potassium thiocyanate) to prepare a variety of amino acid analogs. Two different pathways for ring opening of 17 were elucidated: direct nucleophilic displacement, as well as β-elimination followed by Michael addition. Furthermore, β-keto ester and β-keto ketone products 18k,18m, and 18i were converted to prolines and pyrazole amino acids.Key words: glutamate, amino acid, cyclic sulfamidate, proline.

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Amino acid synthesis via ring opening of N-sulphonyl aziridine-2-carboxylate esters with organometallic reagents.

Tetrahedron ◽

10.1016/s0040-4020(01)87968-0 ◽

1993 ◽

Vol 49 (28) ◽

pp. 6309-6330 ◽

Cited By ~ 73

Author(s):

Jack E. Baldwin ◽

Alan C. Spivey ◽

Christopher J. Schofield ◽

Joseph B. Sweeney

Keyword(s):

Amino Acid ◽

Ring Opening ◽

Acid Synthesis ◽

Amino Acid Synthesis ◽

Organometallic Reagents

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ChemInform Abstract: Amino Acid Synthesis via Ring Opening of N-Sulfonyl Aziridine-2- carboxylate Esters with Organometallic Reagents.

ChemInform ◽

10.1002/chin.199346123 ◽

2010 ◽

Vol 24 (46) ◽

pp. no-no

Author(s):

J. E. BALDWIN ◽

A. C. SPIVEY ◽

C. J. SCHOFIELD ◽

J. B. SWEENEY

Keyword(s):

Amino Acid ◽

Ring Opening ◽

Acid Synthesis ◽

Amino Acid Synthesis ◽

Organometallic Reagents

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Faculty Opinions recommendation of Photoredox activation of carbon dioxide for amino acid synthesis in continuous flow.

Faculty Opinions – Post-Publication Peer Review of the Biomedical Literature ◽

10.3410/f.727212076.793527478 ◽

2017 ◽

Author(s):

Donald Pinto ◽

Kumar Pabbisetty ◽

Vladimir Ladziata

Keyword(s):

Carbon Dioxide ◽

Amino Acid ◽

Continuous Flow ◽

Acid Synthesis ◽

Amino Acid Synthesis

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Petasis vs. Strecker Amino Acid Synthesis: Convergence, Divergence and Opportunities in Organic Synthesis

Molecules ◽

10.3390/molecules26061707 ◽

2021 ◽

Vol 26 (6) ◽

pp. 1707

Author(s):

Wayiza Masamba

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Organic Synthesis ◽

Acid Synthesis ◽

Physical Sciences ◽

Amino Acid Synthesis

α-Amino acids find widespread applications in various areas of life and physical sciences. Their syntheses are carried out by a multitude of protocols, of which Petasis and Strecker reactions have emerged as the most straightforward and most widely used. Both reactions are three-component reactions using the same starting materials, except the nucleophilic species. The differences and similarities between these two important reactions are highlighted in this review.

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