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

2001 ◽  
pp. 1876-1884 ◽  
Author(s):  
Hervé J. C. Deboves ◽  
Christian A. G. N. Montalbetti ◽  
Richard F. W. Jackson
Keyword(s):  
Amino Acids ◽  
Direct Synthesis

scholarly journals Recent Advances in Rapid Synthesis of Non-proteinogenic Amino Acids from Proteinogenic Amino Acids Derivatives via Direct Photo-Mediated C–H Functionalization

Molecules ◽  
2020 ◽  
Vol 25 (22) ◽  
pp. 5270
Author(s):  
Zhenbo Yuan ◽  
Xuanzhong Liu ◽  
Changmei Liu ◽  
Yan Zhang ◽  
Yijian Rao
Keyword(s):  
Amino Acids ◽  
Direct Synthesis ◽  
Environmentally Friendly ◽  
Powerful Method ◽  
Rapid Synthesis ◽  
Conservation Of Energy ◽  
Mild Conditions ◽  
Recent Advances ◽  
Recent Developments

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.

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

2019 ◽  
Vol 21 (3) ◽  
pp. 709-713 ◽  
Author(s):  
Haruki Inada ◽  
Masatoshi Shibuya ◽  
Yoshihiko Yamamoto
Keyword(s):  
Amino Acids ◽  
Direct Synthesis ◽  
Step Process

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

2005 ◽  
Vol 83 (6-7) ◽  
pp. 937-942 ◽  
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.

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

2013 ◽  
Vol 15 (22) ◽  
pp. 5770-5773 ◽  
Author(s):  
Yuttapong Singjunla ◽  
Jérôme Baudoux ◽  
Jacques Rouden
Keyword(s):  
Amino Acids ◽  
Direct Synthesis ◽  
Aldol Reaction

Direct synthesis of unsaturated β-amino acids

2002 ◽  
Vol 662 (1-2) ◽  
pp. 172-177 ◽  
Author(s):  
Moncef Bellassoued ◽  
Jérôme Grugier ◽  
Nathalie Lensen
Keyword(s):  
Amino Acids ◽  
Direct Synthesis

ChemInform Abstract: The Direct Synthesis of Novel Enantiomerically Pure α-Amino Acids in Protected Form via Suzuki Cross-Coupling.

ChemInform ◽  
2000 ◽  
Vol 31 (48) ◽  
pp. no-no
Author(s):  
Philip N. Collier ◽  
Andrew D. Campbell ◽  
Ian Patel ◽  
Richard J. K. Taylor
Keyword(s):  
Amino Acids ◽  
Direct Synthesis ◽  
Cross Coupling ◽  
Enantiomerically Pure

Direct synthesis of .alpha.-halogenomethyl-.alpha.-amino acids from the parent .alpha.-amino acids

1979 ◽  
Vol 44 (15) ◽  
pp. 2732-2742 ◽  
Author(s):  
Philippe Bey ◽  
Jean Paul Vevert ◽  
Viviane Van Dorsselaer ◽  
Michael Kolb
Keyword(s):  
Amino Acids ◽  
Direct Synthesis
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