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Synthesis 2018; 50(20): 4047-4054
DOI: 10.1055/s-0037-1610268
DOI: 10.1055/s-0037-1610268
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Formal (4+1) Cyclization of Ammonium Ylides with Vinylogous para-Quinone Methides
This work was supported by the Austrian Science Funds (FWF): Project No. P26387-N28. The NMR spectrometers used were acquired in collaboration with the University of South Bohemia (CZ) with financial support from the European Union through the EFRE INTERREG IV ETC-AT-CZ program (project M00146, ‘RERI-uasb’).Weitere Informationen
Publikationsverlauf
Received: 07. August 2018
Accepted after revision: 13. August 2018
Publikationsdatum:
05. September 2018 (online)
Abstract
The formal (4+1) cyclization between in situ generated achiral carbonyl-stabilized ammonium ylides and vinylogous p-quinone methides can be carried out under operationally simple conditions, leading to two different double bond regioisomers depending on the conditions used. Apart from these racemic approaches, a first proof-of-concept for enantioselective versions of these reactions was also obtained.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610268.
- Supporting Information
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References
- 1a Coxon DT. Price KR. Howard B. Osman SF. Kalan EB. Zacharius RM. Tetrahedron Lett. 1974; 15: 2921
- 1b Xu K. Jiang J.-S. Feng Z.-M. Yang Y.-N. Li L. Zang C.-X. Zhang P.-C. J. Nat. Prod. 2016; 79: 1567
- 1c Cava MP. Nomura K. Schlessinger RH. Buck KT. Douglas B. Rauffauf RF. Weisbach JA. Chem. Ind. 1964; 282
- 1d Bernauer K. Helv. Chim. Acta 1963; 46: 1783
- 1e Edrada RA. Stessman CC. Crews P. J. Nat. Prod. 2003; 66: 939
- 1f Park HB. Kim Y.-J. Lee JK. Lee KR. Kwon HC. Org. Lett. 2012; 14: 5002
- 1g Du W.-K. Hung H.-Y. Kuo P.-C. Hwang T.-L. Shiu L.-C. Shiu K.-B. Lee E.-J. Tai S.-H. Wu T.-S. Org. Lett. 2016; 18: 3042
- 2a Yoshida M. Nemoto T. Zhao Z. Ishige Y. Hamada Y. Tetrahedron: Asymmetry 2012; 23: 859
- 2b Nemoto T. Matsuo N. Hamada Y. Adv. Synth. Catal. 2014; 356: 2417
- 2c Wu Q.-F. Liu C.-X. Zhuo Z.-Q. Ye K.-Y. You S.-I. Angew. Chem. Int. Ed. 2011; 48: 6293
- 2d Wu WT. Xu RQ. Zhang L. You S.-L. Chem. Sci. 2016; 7: 3427
- 2e Nicolaou KC. Li A. Ellery SP. Edmonds DJ. Angew. Chem. Int. Ed. 2009; 48: 6293
- 2f Yang L. Zheng H. Luo L. Nan J. Liu J. Wang Y. Luan X. J. Am. Chem. Soc. 2015; 137: 4876
- 2g Luo L. Zheng H. Liu J. Wang H. Wang Y. Luan X. Org. Lett. 2016; 18: 2082
- 2h Ma C. Huang Y. Zhao Y. ACS Catal. 2016; 6: 6408
- 3a Yuan Z. Gai K. Wu Y. Wu J. Lin A. Yao H. Chem. Commun. 2017; 53: 3485
- 3b Zhang X.-Z. Deng Y.-H. Gan K.-J. Yan X. Yu K.-Y. Wang F.-X. Fan C.-A. Org. Lett. 2017; 19: 1752
- 4a Zhu C. Ding Y. Ye L.-W. Org. Biomol. Chem. 2015; 13: 2530
- 4b Chen J.-R. Hu X.-Q. Lu L.-A. Xiao W.-J. Chem. Rev. 2015; 115: 5301
- 5 For a review on ammonium ylides, see: Roiser L. Zielke K. Waser M. Asian J. Org. Chem. 2018; 7: 852
- 6a McGarrigle EM. Myers EL. Illa O. Shaw MA. Riches SL. Aggarwal VK. Chem. Rev. 2007; 107: 5841
- 6b Sun X.-L. Tang Y. Acc. Chem. Res. 2008; 41: 937
- 6c Burtoloso AC. B. Dias RM. P. Leonarczyk IA. Eur. J. Org. Chem. 2013; 5005
- 7 Roiser L. Waser M. Org. Lett. 2017; 19: 2338
- 8a Yang Z. Fan M. Liu W. Liang Y. Synthesis 2005; 2188
- 8b Yang Z. Fan M. Mu R. Liu W. Liang Y. Tetrahedron 2005; 61: 9140
- 8c Worgull D. Öhler L. Strache JP. Friedrichs T. Ullrich P. Eur. J. Org. Chem. 2017; 6077
- 8d Midya SP. Gopi E. Satam N. Namboothiri IN. N. Org. Biomol. Chem. 2017; 15: 3616
- 8e Zhu C.-Y. Deng X.-M. Sun X.-L. Zheng J.-C. Tang Y. Chem. Commun. 2008; 738
- 8f Zheng P.-F. Ouyang Q. Niu S.-L. Shuai L. Yuan Y. Jiang K. Liu T.-Y. Chen Y.-C. J. Am. Chem. Soc. 2015; 137: 9390
- 8g Liu L. Yuan Y. Pan R. Zeng Y. Lin A. Yao H. Huang Y. Org. Chem. Front. 2018; 5: 623
- 9 Meisinger N. Roiser L. Monkowius U. Himmelsbach M. Robiette R. Waser M. Chem. Eur. J. 2017; 23: 5137
- 10a Waser M. Herchl R. Müller N. Chem. Commun. 2011; 47: 2170
- 10b Herchl R. Stiftinger M. Waser M. Org. Biomol. Chem. 2011; 9: 7023
- 10c Novacek J. Roiser L. Zielke K. Robiette R. Waser M. Chem. Eur. J. 2016; 22: 11422
- 10d Roiser L. Robiette R. Waser M. Synlett 2016; 27: 1963
- 10e Winter M. Gaunersdorfer C. Roiser L. Zielke K. Monkowius U. Waser M. Eur. J. Org. Chem. 2018; 418
- 11a Goldschmidt Z. Crammer B. Chem. Soc. Rev. 1988; 17: 229
- 11b Hudlicky T. Reed JW. Angew. Chem. Int. Ed. 2010; 49: 4864
- 12 For a recent study where such an approach shed some light on intramolecular double-bond migrations, see: Zielke K. Waser M. Org. Lett. 2018; 20: 768
- 13 Zhu C.-Y. Sun X.-L. Deng X.-M. Zheng J.-C. Tang Y. Tetrahedron 2008; 64: 5583
- 14 Further details can be found in the online Supporting Information.
For reviews on (4+1) cyclizations, see:
For reviews on sulfonium ylides, see:
For ammonium ylide mediated (4+1) cyclizations, see:
For selected examples, see:
For two reviews, see: