Practical Methods for the Synthesis of Symmetrically α,α-Disubstituted α-Amino Acids

被引：127

作者：

Soloshonok, Vadim A. ^{[1
]}

Sorochinsky, Alexander E. ^{[2
]}

机构：

[1] Univ Oklahoma, Dept Chem & Biochem, Norman, OK 73019 USA

[2] Natl Acad Sci Ukraine, Inst Bioorgan Chem & Petrochem, UA-9402660 Kiev, Ukraine

来源：

SYNTHESIS-STUTTGART | 2010年 / 14期

关键词：

sterically constrained; alpha; alpha-disubstituted alpha-amino acids; dialkylation; nucleophilic glycine equivalents; nickel(II) complexes; MICHAEL ADDITION-REACTIONS; NUCLEOPHILIC GLYCINE EQUIVALENTS; EFFICIENT ASYMMETRIC-SYNTHESIS; VIRTUALLY COMPLETE CONTROL; INDUCED AXIAL CHIRALITY; SUBSTITUTED PYROGLUTAMIC ACIDS; ACHIRAL-PHASE CHROMATOGRAPHY; PURE 4-AMINOGLUTAMIC ACIDS; LARGE-SCALE SYNTHESIS; ONE-POT SYNTHESIS;

D O I：

10.1055/s-0029-1220013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This report provides an overview of the practical methods for preparing symmetrically alpha,alpha-disubstituted alpha-amino acids and their derivatives. Despite the growing application of this particular type of sterically constrained alpha-amino acid in the de novo design of peptides and peptidomimetics, synthetically important achievements in the field have not been summarized so far. Classical methods, such as the Bucherer-Bergs and Strecker reactions of sym-dialkyl and cyclic ketones, as well as recent methods involving dialkylation of nucleophilic glycine equivalents and Ugi reactions, are presented.

引用

页码：2319 / 2344

页数：26

共 50 条

[31] Synthesis of α,α-disubstituted-α-amino acids by double nucleophilic addition to cyanohydrins
Charette, AB
Gagnon, A
Janes, M
Mellon, C
TETRAHEDRON LETTERS, 1998, 39 (29) : 5147 - 5150
[32] Synthesis of 3,4-disubstituted pyrrole amino acids.
Mapes, CM
Nemeroff, NH
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 309 - CHEN
[33] Preparation of achiral and of enantiopure geminally disubstituted β-amino acids for β-peptide synthesis
Abele, S
Seebach, D
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (01) : 1 - 15
[34] Synthesis of protected, chiral α,α-disubstituted α-amino acids via a Beckmann rearrangement
Frutos, RP
Spero, DM
TETRAHEDRON LETTERS, 1998, 39 (17) : 2475 - 2478
[35] Recent Advances in Asymmetric Catalytic Methods for the Formation of Acyclic α,α-Disubstituted α-Amino Acids
Metz, Alison E.
Kozlowski, Marisa C.
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01): : 1 - 7
[36] Synthesis of Novel Oxazolyl Amino Acids and Their Use in the Parallel Synthesis of Disubstituted Oxazole Libraries
Murru, Siva
Bista, Ramesh
Nefzi, Adel
SYNTHESIS-STUTTGART, 2018, 50 (07): : 1546 - 1554
[37] METHODS ESTERS SYNTHESIS OF SULFUR AMINO ACIDS
Dzhusupova, K. A.
Ernazarov, K. K.
BULLETIN OF THE NATIONAL ACADEMY OF SCIENCES OF THE REPUBLIC OF KAZAKHSTAN, 2014, (01): : 39 - 42
[38] Stereocontrolled routes to β,β′-disubstituted α-amino acids
Michaux, Julien
Niel, Gilles
Campagne, Jean-Marc
CHEMICAL SOCIETY REVIEWS, 2009, 38 (07) : 2093 - 2116
[39] Efficient Synthesis of Symmetrical α,α-Disubstituted β-Amino Acids and α,α-Disubstituted Aldehydes via Dialkylation of Nucleophilic β-Alanine Equivalent
Lin, Daizong
Deng, Guanghui
Wang, Jiang
Ding, Xiao
Jiang, Hualiang
Liu, Hong
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05): : 1717 - 1722
[40] Enantioselective synthesis of β-amino acids.: Part 10:: Preparation of novel α,α- and β,β-disubstituted β-amino acids from (S)-asparagine
Juaristi, E
Balderas, M
López-Ruiz, H
Jiménez-Pérez, VM
Kaiser-Carril, ML
Ramírez-Quirós, Y
TETRAHEDRON-ASYMMETRY, 1999, 10 (18) : 3493 - 3505

← 1 2 3 4 5 →