Direct Synthesis of β-Hydroxy-α-amino Acids via Diastereoselective Decarboxylative Aldol Reaction

Non-proteinogenic amino acids have attracted tremendous interest for their essential applications in the realm of biology and chemistry. Recently, rising C–H functionalization has been considered an alternative powerful method for the direct synthesis of non-proteinogenic amino acids. Meanwhile, photochemistry has become popular for its predominant advantages of mild conditions and conservation of energy. Therefore, C–H functionalization and photochemistry have been merged to synthesize diverse non-proteinogenic amino acids in a mild and environmentally friendly way. In this review, the recent developments in the photo-mediated C–H functionalization of proteinogenic amino acids derivatives for the rapid synthesis of versatile non-proteinogenic amino acids are presented. Moreover, postulated mechanisms are also described wherever needed.

Download Full-text

Direct synthesis of Fmoc-protected amino acids using organozinc chemistry: application to polymethoxylated phenylalanines and 4-oxoamino acids†

Journal of the Chemical Society Perkin Transactions 1 ◽

10.1039/b103832j ◽

2001 ◽

pp. 1876-1884 ◽

Cited By ~ 27

Author(s):

Hervé J. C. Deboves ◽

Christian A. G. N. Montalbetti ◽

Richard F. W. Jackson

Keyword(s):

Amino Acids ◽

Direct Synthesis

Download Full-text

Nanosheet-Enhanced Asymmetric Induction of Chiral α-Amino Acids in Catalytic Aldol Reaction

Chemistry - A European Journal ◽

10.1002/chem.201202604 ◽

2012 ◽

Vol 18 (48) ◽

pp. 15323-15329 ◽

Cited By ~ 15

Author(s):

Li-Wei Zhao ◽

Hui-Min Shi ◽

Jiu-Zhao Wang ◽

Jing He

Keyword(s):

Amino Acids ◽

Aldol Reaction ◽

Asymmetric Induction

Download Full-text

Asymmetric organocatalysis with glycosyl-β-amino acids: direct asymmetric aldol reaction of acetone with aldehydes

Carbohydrate Research ◽

10.1016/j.carres.2006.08.007 ◽

2006 ◽

Vol 341 (16) ◽

pp. 2737-2743 ◽

Cited By ~ 13

Author(s):

Namrata Dwivedi ◽

Surendra S. Bisht ◽

Rama P. Tripathi

Keyword(s):

Amino Acids ◽

Aldol Reaction ◽

Asymmetric Aldol ◽

Asymmetric Aldol Reaction ◽

Asymmetric Organocatalysis

Download Full-text

Direct Synthesis of Free α-Amino Acids by Telescoping Three-Step Process from 1,2-Diols

Organic Letters ◽

10.1021/acs.orglett.8b03910 ◽

2019 ◽

Vol 21 (3) ◽

pp. 709-713 ◽

Cited By ~ 5

Author(s):

Haruki Inada ◽

Masatoshi Shibuya ◽

Yoshihiko Yamamoto

Keyword(s):

Amino Acids ◽

Direct Synthesis ◽

Step Process

Download Full-text

α-Amino Acids, β-Amino Alcohols and Related Compounds as Chiral Auxiliaries, Ligands and Catalysts in the Asymmetric Aldol Reaction

ChemInform ◽

10.1002/chin.200604254 ◽

2006 ◽

Vol 37 (4) ◽

Author(s):

Jose L. Vicario ◽

Dolores Badia ◽

Luisa Carrillo ◽

Efraim Reyes ◽

Juan Etxebarria

Keyword(s):

Amino Acids ◽

Aldol Reaction ◽

Amino Alcohols ◽

Chiral Auxiliaries ◽

Asymmetric Aldol ◽

Asymmetric Aldol Reaction ◽

Related Compounds

Download Full-text

Direct synthesis of unprotected α-amino acids via allylation of hydroxyglycine

Canadian Journal of Chemistry ◽

10.1139/v05-096 ◽

2005 ◽

Vol 83 (6-7) ◽

pp. 937-942 ◽

Cited By ~ 15

Author(s):

Masaharu Sugiura ◽

Chieko Mori ◽

Keiichi Hirano ◽

Shū Kobayashi

Keyword(s):

Amino Acids ◽

Direct Synthesis ◽

Glyoxylic Acid ◽

Cope Rearrangement ◽

Reaction Conditions ◽

Stereoselective Reactions ◽

High Stereoselectivity

Hydroxyglycine, the ammonia adduct of glyoxylic acid, was found to react with various allylboronates in the presence of triethylamine in methanol to give unprotected α-amino acids directly with high stereoselectivity. For instance, the reactions with (E)- and (Z)-crotylboronates afforded the corresponding anti- and syn-crotylated products (isoleucine and alloisoleucine after hydrogenation) with high diastereoselectivity, respectively. Interestingly, it was found that isomerization of the products (γ-adducts to α-adducts) occurred under the reaction conditions in some cases. Control experiments have suggested that the isomerization took place via 2-aza (or azonia) Cope rearrangement of imines derived from γ-adducts and glyoxylic acid.Key words: hydroxyglycine, glyoxylic acid, allylboronates, α-amino acids, allylglycines, isoleucine, alloisoleucine, stereoselective reactions, isomerization, 2-aza (azonia) Cope rearrangement.

Download Full-text