One-pot, two-step synthesis of unnatural α-amino acids involving the exhaustive aerobic oxidation of 1,2-diols

Abstract

Fluorescent, photoactivatable, and other functional amino acids were efficiently synthesized by a one-pot, two-step protocol.

Asymmetric synthesis of (S)‐α‐(octyl)glycine via alkylation of Ni(II) complex of chiral glycine Schiff base

“…This process was shown to be quite efficient to perform deracemization, dynamic thermodynamic resolution, or (S) to (R) interconversion of unprotected α- [40][41][42] and β-AAs. 43 In this work, we examine the application of this methodology for asymmetric synthesis of (S)-α-(octyl)glycine, [44][45][46][47][48][49] a characteristic representative of naturally occurring class of lipidic α-AAs serving as key structural units in the design of lipophilic analogs of various biologically active peptides, such as enzymes, hormones, and therapeutic drugs. [50][51][52][53][54][55] For this work, we selected tri-dentate ligand 5 (Scheme 2) and the corresponding glycine complex 6, which show enhanced stereocontrolling properties due to a parallel displaced type of aromatic interactions between the selectively chlorinated o-amino-benzophenone and Pro N-benzyl rings.…”

“…This process was shown to be quite efficient to perform deracemization, dynamic thermodynamic resolution, or ( S ) to ( R ) interconversion of unprotected α‐ 40–42 and β‐AAs 43 . In this work, we examine the application of this methodology for asymmetric synthesis of ( S )‐α‐(octyl)glycine, 44–49 a characteristic representative of naturally occurring class of lipidic α‐AAs serving as key structural units in the design of lipophilic analogs of various biologically active peptides, such as enzymes, hormones, and therapeutic drugs 50–55 …”

Alkenylation of ortho-palladated phenylglycine: synthesis of stilbene derivatives and 3-aryl-isoquinoline-1-carboxylates

“…The commonly employed syntheses are restricted to a few strategies that usually involve tedious procedures and/or low conversions. [10] Enzymatic resolution does not provide a definitive solution due to the waste of a proportion of the products obtained, [11][12][13] although biocatalysis does provide an elegant solution. [14][15][16][17] Due to the high value of the final species, the development of efficient alternative procedures is highly desirable.…”

Synthesis of Unprotected 2-Arylglycines by Transamination of Arylglyoxylic Acids with 2-(2-Chlorophenyl)glycine

“…In 1934, Herbst and Engel reported thermally promoted biomimetic transaminations between α-keto acids and 2-phenylglycine without any catalysts to form the corresponding unprotected α-amino acids (Scheme a) . Although related research has been reported, the methods have not been applied to organic synthesis. , Intrigued by the potential usefulness of transamination, we recently reported a modified protocol . Combining transamination with the oxidation of 1,2-diols to α-keto acids, we established a direct method for the synthesis of unprotected α-amino acids.…”