Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2016; 48(18): 3031-3041
DOI: 10.1055/s-0035-1562515
DOI: 10.1055/s-0035-1562515
psp
Practical Synthetic Procedures for the Iron-Catalyzed Intermolecular Olefin Aminohydroxylation Using Functionalized Hydroxylamines
Further Information
Publication History
Received: 02 June 2016
Accepted after revision: 06 June 2016
Publication Date:
25 July 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201618/lookinside/thumbnails/ss-2016-z0354-psp_10-1055_s-0035-1562515-1.jpg)
‡ These authors contributed equally to this study.
Abstract
A set of practical synthetic procedures for the iron-catalyzed intermolecular olefin aminohydroxylation reactions in gram scale is reported. In these transformations, a bench-stable functionalized hydroxylamine is applied as the amination reagent. This method is compatible with a broad range of synthetically valuable olefins including those that are incompatible with the existing aminohydroxylation methods. It also provides valuable amino alcohol building blocks with regio- and stereochemical arrays that are complementary to known methods.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562515.
- Supporting Information
-
References
- 1a Sharpless KB, Chong AO, Oshima K. J. Org. Chem. 1976; 41: 177
- 1b Li GG, Chang HT, Sharpless KB. Angew. Chem., Int. Ed. Engl. 1996; 35: 451
- 2a Fuller PH, Kim J.-W, Chemler SR. J. Am. Chem. Soc. 2008; 130: 17638
- 2b Paderes MC, Chemler SR. Org. Lett. 2009; 11: 1915
- 2c Sequeira FC, Chemler SR. Org. Lett. 2012; 14: 4482
- 2d Michaelis DJ, Shaffer CJ, Yoon TP. J. Am. Chem. Soc. 2007; 129: 1866
- 2e Williamson KS, Yoon TP. J. Am. Chem. Soc. 2010; 132: 4570
- 2f Williamson KS, Yoon TP. J. Am. Chem. Soc. 2012; 134: 12370
- 2g Zhang B, Studer A. Org. Lett. 2013; 15: 4548
- 3a Liu G.-S, Zhang Y.-Q, Yuan Y.-A, Xu H. J. Am. Chem. Soc. 2013; 135: 3343
- 3b Zhang Y.-Q, Yuan Y.-A, Liu G.-S, Xu H. Org. Lett. 2013; 15: 3910
- 3c Lu D.-F, Liu G.-S, Zhu C.-L, Yuan B, Xu H. Org. Lett. 2014; 16: 2912
- 3d Zhu C.-L, Tian J.-S, Gu Z.-Y, Xing G.-W, Xu H. Chem. Sci. 2015; 6: 3044
- 3e Tian J.-S, Zhu C.-L, Chen Y.-R, Xu H. Synthesis 2015; 47: 1709
- 4 Lu D.-F, Zhu C.-L, Jia Z.-X, Xu H. J. Am. Chem. Soc. 2014; 136: 13186
- 5 For detailed synthetic procedures of 2, L1, and L2, see experimental section.
- 6a For a manganese-mediated glycal aziridination for 2-amino sugar synthesis, see: Du Bois J, Tomooka CS, Hong J, Carreira EM. J. Am. Chem. Soc. 1997; 119: 3179
- 6b For a selected indirect method for 2-amino sugar synthesis, see: Griffith DA, Danishefsky SJ. J. Am. Chem. Soc. 1990; 112: 5811
- 7a Masruri, Willis AC, McLeod MD. J. Org. Chem. 2012; 77: 8480
- 7b Corey EJ, Roper TD, Ishihara K, Sarakinos G. Tetrahedron Lett. 1993; 34: 8399
- 8 For experimental details, see Supporting Information.
- 9 Cis/trans isomeric olefins have been observed to present different reactivity and selectivity in atom transfer reactions that proceed via a stepwise mechanism. For a selected reference, see: Lee NH, Jacobsen EN. Tetrahedron Lett. 1991; 32: 6533
- 10 Behr J.-B, Chevrier C, Defoin A, Tarnus C, Streith J. Tetrahedron 2003; 59: 543
- 11 Ng K.-H, Chan AS. C, Yu W.-Y. J. Am. Chem. Soc. 2010; 132: 12862
- 12 Jiang H.-F, Ye J.-W, Qi C.-R, Huang L.-B. Tetrahedron Lett. 2010; 51: 928
- 13 He T, Gao W.-C, Wang W.-K, Zhang C. Adv. Synth. Catal. 2014; 356: 1113
- 14 Endeshaw MM, Bayer A, Hansen LK, Gautun OR. Eur. J. Org. Chem. 2006; 5249
- 15 Gómez-Sánchez E, Soriano E, Marco-Contelles J. J. Org. Chem. 2007; 72: 8656
For selected references of nonprecious metal-catalyzed olefin amino-oxygenation reactions, see:
For intramolecular olefin aminofluorination and aminohalogenation via iron-nitrenoid intermediates, see:
For osmium-based aminohydroxylation of indene affords racemic mixtures of 1-, and 2-amino indanols, see:
For an indirect method of 2-aminoindanol synthesis, see: