Recent Developments in the Synthesis of Fluorine-Containing β-Amino Acids and β-Lactams

被引：7

作者：

Lin, Daizong ^{[1
]}

Wang, Jiang ^{[1
]}

Liu, Hong ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 33卷 / 10期

基金：

中国国家自然科学基金;

关键词：

fluorine-containing beta-amino acid; fluorine-containing beta-lactam; synthesis; CONVENIENT ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; (R)-3-AMINO-4,4,4-TRIFLUOROBUTANOIC ACID; RHODOPEPTIN ANALOGS; ANTIFUNGAL ACTIVITY; ESTERS; REFORMATSKY; ENANTIOPURE; DERIVATIVES;

D O I：

10.6023/cjoc201303020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fluorine-containing beta-amino acids and beta-lactams have attracted appreciable attention due to their wide application in organic chemistry, drug discovery, and protein biology. Accordingly, the development of efficient synthetic methods is of considerable interest in academia and industry. The synthesis and resolution are achieved. This review briefly summarizes the recent development in the methodologies for the synthesis of fluorine-containing beta-amino acids and beta-lactams with classification by the species of the fluorine-containing beta-amino acids (alpha-fluorinated beta-amino acids, alpha-trifluoromethyl beta-amino acids, and beta-trifluoromethyl beta-amino acids).

引用

收藏

页码：2098 / 2107

页数：10

相关论文

共 60 条

[41] Synthesis of fluorinated amino acids [J].

Qiu, XL ;

Meng, WD ;

Qing, FL .

TETRAHEDRON, 2004, 60 (32) :6711-6745

[42] Synthesis of fluorinated α,β-diamino esters by ring opening of activated 3-trifluoromethyl-aziridine-2-carboxylates [J].

Rinaudo, G ;

Narizuka, S ;

Askari, N ;

Crousse, B ;

Bonnet-Delpon, D .

TETRAHEDRON LETTERS, 2006, 47 (13) :2065-2068

[43] Discovery of 1-(4-fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)-hydroxypropyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone (SCH 58235):: A designed, potent, orally active inhibitor of cholesterol absorption [J].

Rosenblum, SB ;

Huynh, T ;

Afonso, A ;

Davis, HR ;

Yumibe, N ;

Clader, JW ;

Burnett, DA .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (06) :973-980

[44] The simple and selective synthesis of 3-amino-2,2-difluorocarboxylic esters and difluoro-β-lactams using ethyl bromodifluoroacetate in the presence of rhodium catalyst [J].

Sato, K ;

Tarui, A ;

Matsuda, S ;

Omote, M ;

Ando, A ;

Kumadaki, I .

TETRAHEDRON LETTERS, 2005, 46 (45) :7679-7681

[45] An improved approach to trifluoromethyl substituted Morita-Baylis-Hillman adduct:: Fluorinated dehydro-β-amino acids [J].

Sergeeva, NN ;

Golubev, AS ;

Hennig, L ;

Findeisen, M ;

Paetzold, E ;

Oehme, G ;

Burger, K .

JOURNAL OF FLUORINE CHEMISTRY, 2001, 111 (01) :41-44

[46]

Sergeeva NN, 2001, SYNTHESIS-STUTTGART, P281

[47] First highly stereoselective synthesis of anti-α-trifluoromethyl-β-amino acid derivatives [J].

Shimada, Taichi ;

Yoshioka, Masamitsu ;

Konno, Tsutomu ;

Ishihara, Takashi .

CHEMICAL COMMUNICATIONS, 2006, (34) :3628-3630

[48] Convenient, large-scale asymmetric synthesis of β-aryl-substituted α,α-difluoro-β-amino acids [J].

Soloshonok, VA ;

Ohkura, H ;

Sorochinsky, A ;

Voloshin, N ;

Markovsky, A ;

Belik, M ;

Yamazaki, T .

TETRAHEDRON LETTERS, 2002, 43 (31) :5445-5448

[49] Highly enantioselective transfer of chirality from a less to a more configurationally unstable stereogenic center. A practical asymmetric synthesis of (fluoroalkyl)amines via biomimetic transamination [J].

Soloshonok, VA ;

Ono, T .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10) :3030-3031

[50] Operationally convenient asymmetric synthesis of (S)- and (R)-3-amino-4,4,4-trifluorobutanoic acid -: Part I:: Enantioselective biomimetic transamination of isopropyl 4,4,4-trifluoro-3-oxo-butanoate [J].

Soloshonok, Vadim A. ;

Ohkura, Hironari ;

Yasumoto, Manabu .

JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (07) :924-929

← 1 2 3 4 5 6 →