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Synthesis 2018; 50(17): 3337-3343
DOI: 10.1055/s-0037-1609580
DOI: 10.1055/s-0037-1609580
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Synthesis of Isothiocineole and Application in Multigram-Scale Sulfur Ylide Mediated Asymmetric Epoxidation and Aziridination
This publication is based on work supported by the University of Bristol, the Irish Research Council (GOIPG/2014/528), Science Foundation Ireland, and the Marie-Curie Action COFUND (11/SIRG/B2154).fundi
Weitere Informationen
Publikationsverlauf
Received: 18. Juni 2018
Accepted: 21. Juni 2018
Publikationsdatum:
19. Juli 2018 (online)
Abstract
The synthesis of the chiral sulfide isothiocineole from limonene and elemental sulfur on multi-gram scale and its alkylation to make >50 g of the corresponding benzylsulfonium salt are described. The application of this salt to the sulfur ylide-mediated asymmetric epoxidation of aldehydes and the asymmetric aziridination of imines on a >5 g scale is demonstrated.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609580.
- Supporting Information
Primary Data
- for this article are available online at https://doi.org/10.1055/s-0037-1609580 and can be cited using the following DOI: 10.4125/pd0099th.
- Primary Data
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References
- 1a McGarrigle EM. Myers EL. Illa O. Shaw MA. Riches SL. Aggarwal VK. Chem. Rev. 2007; 107: 5841
- 1b Aggarwal VK. McGarrigle EM. Shaw MA. In Science of Synthesis, Stereoselective Synthesis 2: Stereoselective Reactions of Carbonyl and Imino Groups . Molander GA. Georg Thieme Verlag; Stuttgart: 2011. Chap. 2.6, 311
- 1c Brière J.-F. Metzner P. In Organosulfur Chemistry in Asymmetric Synthesis . Toru T. Bolm C. Wiley-VCH; Weinheim: 2009. Chap. 5
- 2 Illa O. Namutebi M. Saha C. Ostovar M. Chen CC. Haddow MF. Nocquet-Thibault S. Lusi M. McGarrigle EM. Aggarwal VK. J. Am. Chem. Soc. 2013; 135: 11951
- 3 Illa O. Arshad M. Ros A. McGarrigle EM. Aggarwal VK. J. Am. Chem. Soc. 2010; 132: 1828
- 4a Brichacek M. Villalobos MN. Plichta A. Njardarson JT. Org. Lett. 2011; 13: 1110
- 4b Brucks AP. Treitler DS. Liu S.-A. Snyder SA. Synthesis 2013; 45: 1886
- 4c Midura WH. Ścianowski J. Banach A. Zając A. Tetrahedron: Asymmetry 2014; 25: 1488
- 4d Luo J. Wu B. Chen M.-W. Jiang G.-F. Zhou Y.-G. Org. Lett. 2014; 16: 2578
- 4e Rousseau O. Delaunay T. Dequirez G. Trieu-Van T. Robeyns K. Robiette R. Chem. Eur. J. 2015; 21: 12899
- 4f Bigot A. Bouchard H. Brun M.-P. Clerc F. Zhang J. Patent PCT Int. Appl. WO 2017076998, 2017
- 4g Liu L. Yuan Z. Pan R. Zeng Y. Lin A. Yao H. Huang Y. Org. Chem. Front. 2018; 5: 623
- 4h Li Q.-Z. Zhang X. Zeng R. Dai Q.-S. Liu Y. Shen X.-D. Leng H.-J. Yang K.-C. Li J.-L. Org. Lett. 2018; 20: 3700
- 4i Cole CJ. F. Chi HM. DeBacker KC. Snyder SA. Synthesis 2018; 50: efirst, DOI: 10.1055/s-0037-1609754
- 4j Luo J. Wu B. Chen M.-W. Jiang G.-F. Zhou Y.-G. Org. Lett. 2014; 16: 2578
- 4k Yuan Z. Fang X. Li X. Wu J. Yao H. Lin A. J. Org. Chem. 2015; 80: 11123
- 5 Weitkamp AW. J. Am. Chem. Soc. 1959; 81: 3430
- 6a Nakatsuchi A. J. Soc. Chem. Ind. Japan (Suppl. Binding) 1930; 33: 408
- 6b Nakatsuchi A. J. Soc. Chem. Ind. Japan (Suppl. Binding) 1932; 35: 376
- 7 Lowe MA. Ostovar M. Ferrini S. Chen CC. Lawrence PG. Fontana F. Calabrese AA. Aggarwal VK. Angew. Chem. Int. Ed. 2011; 50: 6370
- 8 Armarego WL. F. Chai CL. L. Purification of Laboratory Chemicals . 6th ed. Butterwoth-Heinemann; Oxford: 2009: 245
- 9 Reeves JT. Visco MD. Marsini MA. Grinberg N. Busacca CA. Mattson AE. Senanayake CH. Org. Lett. 2015; 17: 2442
- 10a Lanigan R. Starkov P. Sheppard T. J. Org. Chem. 2013; 78: 4515
- 10b Starkov P. Sheppard T. Org. Biomol. Chem. 2010; 5: 1320
- 11 Menger F. Elrington AR. J. Am. Chem. Soc. 1991; 113: 9621
- 12 Berti G. Botari F. Ferrarini PL. Macchia BJ. J. Org. Chem. 1965; 30: 4091
- 13 Fox D. Pedersen D. Petersen A. Warren S. Org. Biomol. Chem. 2006; 4: 3117