Intramolecular, Visible-Light-Mediated Aza Paterno-Buchi Reactions of Unactivated Alkenes

被引:29
作者
Blackmun, Dominique E. [1 ]
Chamness, Stephen A. . [1 ]
Schindler, Corinna S. [1 ]
机构
[1] Univ Michigan, Dept Chem, Willard Henry Dow Lab, Ann Arbor, MI 48109 USA
关键词
AZETIDINES;
D O I
10.1021/acs.orglett.2c01008
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Azetidines are of particular interest in medicinal chemistry for their favorable properties, including increased resistance to oxidative metabolism and lower lipophilicity. The recent development of [2 + 2] reactions has significantly expanded the limited repertoire of methods for azetidine synthesis, but access to more complex architectures still requires further development. Herein, we report a visible-light-enabled intramolecular [2 + 2] cycloaddition of unactivated alkenes that proved previously unreactive to access tricyclic azetidines with 3D complex structures and high levels of saturation.
引用
收藏
页码:3053 / 3057
页数:5
相关论文
共 27 条
[1]   Recent advances in the chemistry of metallated azetidines [J].
Antermite, Daniele ;
Degennaro, Leonardo ;
Luisi, Renzo .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (01) :34-50
[2]   Put a ring on it: application of small aliphatic rings in medicinal chemistry [J].
Bauer, Matthias R. ;
Di Fruscia, Paolo ;
Lucas, Simon C. C. ;
Michaelides, Iacovos N. ;
Nelson, Jennifer E. ;
Storer, R. Ian ;
Whitehurst, Benjamin C. .
RSC MEDICINAL CHEMISTRY, 2021, 12 (04) :448-471
[3]   Synthesis of azetidines via visible-light-mediated intermolecular [2+2] photocycloadditions [J].
Becker, Marc R. ;
Wearing, Emily R. ;
Schindler, Corinna S. .
NATURE CHEMISTRY, 2020, 12 (10) :898-+
[4]   Functionalized azetidines via visible light-enabled aza Paterno-Buchi reactions [J].
Becker, Marc R. ;
Richardson, Alistair D. ;
Schindler, Corinna S. .
NATURE COMMUNICATIONS, 2019, 10 (1)
[5]   Novel syntheses of azetidines and azetidinones [J].
Brandi, Alberto ;
Cicchi, Stefano ;
Cordero, Franca M. .
CHEMICAL REVIEWS, 2008, 108 (09) :3988-4035
[6]   Triazole oxytocin antagonists: Identification of an aryloxyazetidine replacement for a biaryl substituent [J].
Brown, Alan ;
Brown, T. Bruce ;
Calabrese, Andrew ;
Ellis, Dave ;
Puhalo, Nicholas ;
Ralph, Michael ;
Watson, Lesa .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (02) :516-520
[7]  
Collins KD, 2013, NAT CHEM, V5, P597, DOI [10.1038/NCHEM.1669, 10.1038/nchem.1669]
[8]   AZETIDINES - RECENT SYNTHETIC DEVELOPMENTS [J].
CROMWELL, NH .
CHEMICAL REVIEWS, 1979, 79 (04) :331-358
[9]   The Paterno-Buchi reaction - a comprehensive review [J].
D'Auria, Maurizio .
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2019, 18 (10) :2297-2362
[10]   7-Sulfonamido-3-benzazepines as potent and selective 5-HT2C receptor agonists: Hit-to-lead optimization [J].
Fish, Paul V. ;
Brown, Alan D. ;
Evrard, Edel ;
Roberts, Lee R. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (07) :1871-1875