33.4. 2.3 1-Nitrosoalkenes (Update 2015)
Book
Editors: Aitken, R. A.; Brønsted Nielsen, M.; Drabowicz, J.; Li, J. J.; Plietker, B. J.; Wirth, T.
Title: Knowledge Updates 2015/2
Print ISBN: 9783131984616; Online ISBN: 9783131975812; Book DOI: 10.1055/b-003-125870
1st edition © 2016 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Knowledge Updates
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Molander, G. A.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.
Type: Multivolume Edition
Abstract
This chapter deals with the generation of nitrosoalkenes from suitable precursors and their application as synthetically useful key intermediates in organic synthesis, including the synthesis of natural products and biologically active compounds. This is an update to Section 33.4.2, covering selected relevant literature that has been reported since 2007.
Key words
nitrosoalkenes - dehydrohalogenation - halooximes - nitroalkene reduction - [4 + 2] cycloaddition - [3 + 2] cycloaddition - hetero-Diels–Alder - N-hydroxypyrroles - natural products- 12 Trujillo JI, Meyers MJ, Anderson DR, Hegde S, Mahoney MW, Vernier WF, Buchler IP, Wu KK, Yang S, Hartmann SJ, Reitz DB. Bioorg. Med. Chem. Lett. 2007; 17: 4657
- 20 Yang H.-T, Ruan X.-J, Miao C.-B, Xi H.-T, Jiang Y, Meng Q, Sun X.-Q. Tetrahedron Lett. 2009; 50: 7337
-
21 Zimmer R, Buchholz M, Collas M, Angermann J, Homann K, Reissig H.-U. Eur. J. Org. Chem. 2010; 4111
- 31 Feng Y, Majireck MM, Weinreb SM. Angew. Chem. 2012; 124: 13 018 Angew. Chem. Int. Ed. 2012; 51: 12 846
- 32 Nunes SCC, Lopes SMM, Gomes CSB, Lemos A, Pais AACC, Pinho e Melo TMVD. J. Org. Chem. 2014; 79: 10 456
- 34 Krasnikov PE, Sidnin EA, Osyanin VA, Klimochkin YuN. Chem. Heterocycl. Compd. (Engl. Transl.) 2014; 50: 1090
- 37 Yang H.-T, Ren W.-L, Ruan X.-J, Tian Z.-Y, Liang X.-C, Han C, Sun X.-Q, Miao C.-B. Tetrahedron Lett. 2013; 54: 1428
- 50 Durchschein K, Fabian WMF, Macheroux P, Zangger K, Trimmel G, Faber K. Org. Biomol. Chem. 2011; 9: 3364
- 51 Rajawinslin RR, Raihan MJ, Janreddy D, Kavala V, Kuo C.-W, Kuo T.-S, Chen M.-L, He C.-H, Yao C.-F. Tetrahedron 2014; 70: 7505
-
52 Rajawinslin RR, Raihan MJ, Janreddy D, Kavala V, Kuo C.-W, Kuo T.-S, Chen M.-L, He C.-H, Yao C.-F. Eur. J. Org. Chem. 2013; 5743
- 53 Raihan MJ, Rajawinslin RR, Kavala V, Kuo C.-W, Kuo T.-S, He C.-H, Huang H.-N, Yao C.-F. J. Org. Chem. 2013; 78: 8872
-
56 Sukhorukov AYu, Lesiv AV, Eliseev OL, Khomutova YA, Ioffe SL, Borissova AO. Eur. J. Org. Chem. 2008; 4025
- 57 Zimmer R, Schmidt E, Andrä M, Duhs M.-A, Linder I, Reissig H.-U. Beilstein J. Org. Chem. 2009; 5: 44