Improved synthesis of proline-derived Ni(II) complexes of glycine:: Versatile chiral equivalents of nucleophilic glycine for general asymmetric synthesis of α-amino acids

被引：86

作者：

Ueki, H ^{[1
]}

Ellis, TK ^{[1
]}

Martin, CH ^{[1
]}

Boettiger, TU ^{[1
]}

Bolene, SB ^{[1
]}

Soloshonok, VA ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 18期

关键词：

D O I：

10.1021/jo0301494

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetically practical and operationally convenient method for preparing (S)-2-[N-(N-benzylprolyl)-amino] benzophenone (BPBP) and hitherto unknown (S)-2-[N-(N'-benzylprolyl)amino]-4-methylbenzophenone (4-MeBPBP), (S)-2-[N-(N'-benzylprolyl)amino]-5-nitrobenzophenone (5-NO2-BPBP), and their corresponding Ni(II) complexes with glycine [GlyNi(II)BPBP], a widely used chiral equivalent of nucleophilic glycine, and new analogues [GlyNi(II)4-Me-BPBP] and [GlyNi(II)-5- NO2-BPBP] is described. The key step of the method is the synthetically efficient amid bond formation between the corresponding o-aminobenzophenones, featuring significant steric shielding and low nucleophilicity of the amino functionality as well as sterically constrained (S)-N-benzylproline (BP).

引用

页码：7104 / 7107

页数：4

共 50 条

[11] Apply Ni(II) complexes to efficient asymmetric synthesis of chiral α- and β-amino acids
Wang, Jiang
Liu, Hong
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
[12] Synthesis of bis-α,α′-amino acids through diastereoselective bis-alkylations of chiral Ni(II)-complexes of glycine
Wang, Jiang
Liu, Hong
Luis Acena, Jose
Houck, Daniel
Takeda, Ryosuke
Moriwaki, Hiroki
Sato, Tatsunori
Soloshonok, Vadim A.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (27) : 4508 - 4515
[13] COMPLEXES OF NI(II) SCHIFFS BASES OF GLYCINE AND ALANINE WITH (S)-N-(ALPHA-NAPHTHYLMETHYL)PROLINE DERIVATIVES FOR ASYMMETRIC SYNTHESIS OF AMINO-ACIDS
BELOKON, YN
MALEEV, VI
SAPOROVSKAYA, MB
BAKHMUTOV, VI
TIMOFEEVA, TV
BATSANOV, AS
STRUCHKOV, YT
BELIKOV, VM
KOORDINATSIONNAYA KHIMIYA, 1988, 14 (11): : 1565 - 1575
[14] Design, synthesis, and evaluation of a new generation of modular nucleophilic glycine equivalents for the efficient synthesis of sterically constrained α-amino acids
Ellis, Trevor K.
Ueki, Hisanori
Yamada, Takeshi
Ohfune, Yasufumi
Soloshonok, Vadim A.
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (22): : 8572 - 8578
[15] Synthesis and evaluation of a new generation of highly acidic nucleophilic glycine equivalents for the preparation of unnatural α-amino acids
Bergagnini, Mackenzie C.
Ellis, Trevor K.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
[16] Asymmetric synthesis of (S)-α-(octyl)glycine via alkylation of Ni(II) complex of chiral glycine Schiff base
Fu, Bo
Takeda, Ryosuke
Zou, Yupiao
Konno, Hiroyuki
Moriwaki, Hiroki
Abe, Hidenori
Han, Jianlin
Izawa, Kunisuke
Soloshonok, Vadim A.
CHIRALITY, 2020, 32 (12) : 1354 - 1360
[17] New chiral NiII complexes of Schiff's bases of glycine and alanine for efficient asymmetric synthesis of α-amino acids
Saghiyan, AS
Dadayan, SA
Petrosyan, SG
Manasyan, LL
Geolchanyan, AV
Djamgaryan, SM
Andreasyan, SA
Maleev, VI
Khrustalev, VN
TETRAHEDRON-ASYMMETRY, 2006, 17 (03) : 455 - 467
[18] ASYMMETRIC-SYNTHESIS OF ALPHA-METHYLAMINOACIDS BY THE ALKYLATION OF GLYCINE, ALANINE, AND PHENYLALANINE IN CHIRAL NI(II) COMPLEXES
BELOKON, YN
CHERNOGLAZOVA, NI
BAKHMUTOV, VI
GARBALINSKAYA, NS
BELIKOV, VM
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1987, 36 (12): : 2595 - 2601
[19] Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases; Part 1: alkyl halide alkylations
Alexander E. Sorochinsky
José Luis Aceña
Hiroki Moriwaki
Tatsunori Sato
Vadim A. Soloshonok
Amino Acids, 2013, 45 : 691 - 718
[20] Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases; Part 1: alkyl halide alkylations
Sorochinsky, Alexander E.
Luis Acena, Jose
Moriwaki, Hiroki
Sato, Tatsunori
Soloshonok, Vadim A.
AMINO ACIDS, 2013, 45 (04) : 691 - 718

← 1 2 3 4 5 →