Selective Carbon-Carbon Bond Cleavage of Cyclopropylamine Derivatives

被引:124
作者
Sokolova, Olga O. [1 ]
Bower, John F. [1 ,2 ]
机构
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
[2] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England
基金
欧洲研究理事会;
关键词
DONOR-ACCEPTOR CYCLOPROPANES; AMINO-SUBSTITUTED CYCLOPROPANES; INTERMOLECULAR 3+2 ANNULATION; RADICAL-CATION; N-DEALKYLATION; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CATALYZED OXIDATION; RING-EXPANSION; EASY ACCESS;
D O I
10.1021/acs.chemrev.0c00166
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This review summarizes synthetic developments reported from 1987 to 2019 that exploit C-C single bond cleavage of cyclopropylamine-based systems. The synthetic and mechanistic aspects of key methodologies are highlighted, and examples where aminocyclopropanes are exploited as key intermediates in multistep synthesis are also discussed. The review encompasses cases where aminocyclopropanes participate in polar reactions, pericyclic processes, radical-based reactions, and C-C bond activations.
引用
收藏
页码:80 / 109
页数:30
相关论文
共 249 条
[91]   Radical deoxygenation of 3-azatricyclo[2.2.1.02,6]heptan-5-ols to 1,2-dihydropyridines [J].
Hodgson, DM ;
Jones, ML ;
Maxwell, CR ;
Ichihara, O ;
Matthews, IR .
SYNLETT, 2005, (02) :325-327
[92]   6-Substituted 2-azabicyclo[2.2.1]hept-5-enes by nitrogen-directed radical rearrangement: Synthesis of an epibatidine analogue with high binding affinity at the nicotinic acetylcholine receptor [J].
Hodgson, DM ;
Maxwell, CR ;
Wisedale, R ;
Matthews, IR ;
Carpenter, KJ ;
Dickenson, AH ;
Wonnacott, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (23) :3150-3158
[93]   An epoxide rearrangement-radical rearrangement approach to 6-substituted 2-azabicyclo[2.2.1]-5-heptenes: Synthesis of an epibatidine analogue [J].
Hodgson, DM ;
Maxwell, CR ;
Matthews, IR .
SYNLETT, 1998, (12) :1349-1350
[94]   METABOLISM OF 1-AMINOCYCLOPROPANE-1-CARBOXYLIC ACID [J].
HONMA, M ;
SHIMOMURA, T .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1978, 42 (10) :1825-1831
[95]   ENZYMATIC DEAMINATION OF (+/-)-2-METHYL-1-AMINOCYCLOPROPANE-1-CARBOXYLIC AND (S)-2,2-DIMETHYL-1-AMINOCYCLOPROPANE-1-CARBOXYLIC ACID [J].
HONMA, M ;
KIRIHATA, M ;
UCHIMURA, Y ;
ICHIMOTO, I .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1993, 57 (04) :659-661
[96]   Total Synthesis of (±)-Lundurine B [J].
Hoshi, Masaki ;
Kaneko, Osamu ;
Nakajima, Masaya ;
Arai, Shigeru ;
Nishida, Atsushi .
ORGANIC LETTERS, 2014, 16 (03) :768-771
[97]   From Discovery to Application: 50 Years of the Vinylcyclopropane-Cyclopentene Rearrangement and Its Impact on the Synthesis of Natural Products [J].
Hudlicky, Tomas ;
Reed, Josephine W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (29) :4864-4876
[98]   1.3-DIPOLAR CYCLOADDITIONS .65. QUESTION OF A PRIMARY 1.1-ADDITION FOR CYCLOADDITIONS OF NITRILIUM AND DIAZONIUM BETAINES [J].
HUISGEN, R ;
SUSTMANN, R ;
BUNGE, K .
CHEMISCHE BERICHTE-RECUEIL, 1972, 105 (04) :1324-&
[99]   Rhodium(III)-Catalyzed C-H Activation Mediated Synthesis of Isoquinolones from Amides and Cyclopropenes [J].
Hyster, Todd K. ;
Rovis, Tomislav .
SYNLETT, 2013, 24 (14) :1842-1844
[100]   SYNTHETIC STUDIES TOWARD (+)-LYSERGIC ACID: CONSTRUCTION OF THE TETRACYCLIC ERGOLINE SKELETON [J].
Inoue, Tohru ;
Yokoshima, Satoshi ;
Fukuyama, Tohru .
HETEROCYCLES, 2009, 79 :373-378