An Efficient Method for the Reduction of N-Protected Amino Acids and Peptides to the Corresponding Alcohols

A simple and efficient method for the synthesis of N,N’-orthogonally protected imide tethered peptidomimetics is presented. The imide peptidomimetics were synthesized by coupling the in situ generated selenocarboxylate of Nα-protected amino acids with Nα-protected amino acid azides in good yields.

Download Full-text

An Efficient Method for the Reduction of N-Protected Amino Acids and Peptides to the Corresponding Alcohols

Journal of Chemical Research Synopses ◽

10.1039/a902069a ◽

1999 ◽

pp. 424-425 ◽

Cited By ~ 11

Author(s):

T. Naqvi ◽

M. Bhattacharya ◽

W. Haq

Keyword(s):

Amino Acids ◽

Efficient Method

Download Full-text

A Mild and Efficient Method for Copper-Catalyzed Ullmann-Type N-Arylation of Aliphatic Amines and Amino Acids.

ChemInform ◽

10.1002/chin.200748062 ◽

2007 ◽

Vol 38 (48) ◽

Author(s):

Qun Jiang ◽

Deshou Jiang ◽

Yuyang Jiang ◽

Hua Fu ◽

Yufen Zhao

Keyword(s):

Amino Acids ◽

Efficient Method ◽

Aliphatic Amines

Download Full-text

Tandem Radical Decarboxylation−Oxidation of Amino Acids: A Mild and Efficient Method for the Generation ofN-Acyliminium Ions and Their Nucleophilic Trapping

The Journal of Organic Chemistry ◽

10.1021/jo000356t ◽

2000 ◽

Vol 65 (16) ◽

pp. 4930-4937 ◽

Cited By ~ 76

Author(s):

Alicia Boto ◽

Rosendo Hernández ◽

Ernesto Suárez

Keyword(s):

Amino Acids ◽

Efficient Method ◽

Acyliminium Ions ◽

Nucleophilic Trapping

Download Full-text

An Efficient Method for Large-Scale Synthesis of Stereochemically Defined and Conformationally Constrained β-Substituted or α,β-Disubstituted Amino Acids

Peptides: The Wave of the Future ◽

10.1007/978-94-010-0464-0_7 ◽

2001 ◽

pp. 26-27

Author(s):

Xuejun Tang ◽

Vadim A. Soloshonok ◽

Victor J. Hruby

Keyword(s):

Amino Acids ◽

Efficient Method ◽

Large Scale ◽

Conformationally Constrained ◽

Large Scale Synthesis ◽

Disubstituted Amino Acids

Download Full-text

Memory of Chirality of Tertiary Aromatic Amides: A Simple and Efficient Method for the Enantioselective Synthesis of Quaternary α-Amino Acids

Journal of the American Chemical Society ◽

10.1021/ja9039604 ◽

2009 ◽

Vol 131 (30) ◽

pp. 10711-10718 ◽

Cited By ~ 54

Author(s):

Mathieu Branca ◽

Sébastien Pena ◽

Régis Guillot ◽

Didier Gori ◽

Valérie Alezra ◽

...

Keyword(s):

Amino Acids ◽

Efficient Method ◽

Enantioselective Synthesis ◽

Memory Of Chirality

Download Full-text

An Efficient Method for Constructing Cyclic β-Amino Acids Bearing Quaternary Stereocenters

Synlett ◽

10.1055/s-0037-1611718 ◽

2019 ◽

Vol 30 (05) ◽

pp. 593-599 ◽

Cited By ~ 3

Author(s):

Shende Jiang ◽

Guang Yang ◽

Shuanglin Qin ◽

Tongtong Liu ◽

Yunhao Luo ◽

...

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Efficient Method ◽

Ester Group ◽

Chiral Auxiliary ◽

Allyl Ester ◽

Stereogenic Centers ◽

Quaternary Stereocenters ◽

High Yields ◽

Quaternary Stereogenic Centers

This paper describes an efficient method for constructing cyclic β-amino acids bearing quaternary stereocenters. NaHMDS-promoted asymmetric α-alkylation was employed to obtain the key intermediates with quaternary stereogenic centers, which were subsequently reduced by NaBH4 in 10% methanol in THF, with high yields and high diastereoselectivities. By removing the allyl ester group and the chiral auxiliary, the corresponding cyclic β-amino acid hydrochlorides were finally obtained.

Download Full-text

Asymmetric Synthesis of Enantiomerically Enriched a-Amino Acids Containing 2-Furyl- and 2-Thienyl-1,2,4-triazoles in the Side-Chain

Zeitschrift für Naturforschung B ◽

10.5560/znb.2014-3221 ◽

2014 ◽

Vol 69 (4) ◽

pp. 451-460 ◽

Cited By ~ 7

Author(s):

Ashot S. Saghyan ◽

Hayarpi M. Simonyan ◽

Satenik G. Petrosyan ◽

Anna F. Mkrtchyan ◽

Lilit V. Khachatryan ◽

...

Keyword(s):

Amino Acids ◽

Schiff Base ◽

Asymmetric Synthesis ◽

Efficient Method ◽

Enantiomeric Excess ◽

Side Chain ◽

Chiral Auxiliaries ◽

Enantiomerically Pure ◽

Dehydroamino Acids ◽

Hydrolysis Of

An efficient method for the asymmetric synthesis of a-amino acids, containing furyl- and thiophenyl-substituted triazoles in their side-chain, is reported. The strategy relies on Michael addition of 3,4,5-substituted 1,2,4-triazoles to the C=C bond of chiral NiII complexes containing the Schiff base formed from dehydroamino acids (dehydroalanine and (E + Z)-dehydroaminobutyric acid) and from chiral auxiliaries, i. e. (S)-2-N-(N0-benzylprolyl)aminobenzophenone and (S)-2-N- (N0-2-chlorobenzylprolyl) aminobenzophenone. The reactions proceeded with good to very good diastereoselectivity. Hydrolysis of the diastereomeric mixtures of metal complexes afforded the enantiomerically pure a-amino acids with high enantiomeric excess (ee> 98%).

Download Full-text