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. 2018 Oct 3;8(59):34000-34003.
doi: 10.1039/c8ra04325f. eCollection 2018 Sep 28.

Organocatalytic sulfa-Michael/aldol cascade: constructing functionalized 2,5-dihydrothiophenes bearing a quaternary carbon stereocenter

Xiao-Yu Zhu  1 , Mei-Heng Lv  1 , Ya-Nan Zhao  1 , Li-Yan Lan  1 , Wen-Ze Li  1 , Lin-Jiu Xiao  1
Affiliations

Organocatalytic sulfa-Michael/aldol cascade: constructing functionalized 2,5-dihydrothiophenes bearing a quaternary carbon stereocenter

Xiao-Yu Zhu et al. RSC Adv. .

Abstract

A practical sulfa-Michael/aldol cascade reaction of 1,4-dithiane-2,5-diol and α-aryl-β-nitroacrylates has been developed, which allows efficient access to functionalized 2,5-dihydrothiophenes bearing a quaternary carbon stereocenter in moderate to good yields with high enantioselectivities.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. The organocatalysts tested in this study.
Scheme 1
Scheme 1. Proposed transition state and the X-ray structure of 3a.
Fig. 2
Fig. 2. Optimized structures and free energy gap of the transition states.
See this image and copyright information in PMC

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References

    1. Acharya A. Parameshwarappa G. Saraiah B. Ila H. J. Org. Chem. 2015;80:414. doi: 10.1021/jo502429c. - DOI - PubMed
    2. Acharya A. Gautam V. Ila H. J. Org. Chem. 2017;82:7920. doi: 10.1021/acs.joc.7b01153. - DOI - PubMed
    1. Rogers E. Araki H. Batory L. A. Mclnnis C. E. Njardarson J. T. J. Am. Chem. Soc. 2007;129:2768. doi: 10.1021/ja069059h. - DOI - PubMed
    2. McGarraugh P. G. Brenner S. E. Org. Lett. 2009;11:5654. doi: 10.1021/ol9024293. - DOI - PMC - PubMed
    3. Benetti S. De Risi C. Pollini G. P. Zanirato V. Chem. Rev. 2012;112:2129. doi: 10.1021/cr200298b. - DOI - PubMed
    4. De Risi C. Benetti S. Fogagnolo M. Bertolasi V. Tetrahedron Lett. 2013;54:283. doi: 10.1016/j.tetlet.2012.10.134. - DOI
    5. Zaghi A. Bernardi T. Bertolasi V. Bortolini O. Massi A. De Risi C. J. Org. Chem. 2015;80:9176. doi: 10.1021/acs.joc.5b01607. - DOI - PubMed
    1. Spagnol G. Heck M.-P. Nolan S. P. Mioskowski C. Org. Lett. 2002;4:1767. doi: 10.1021/ol025834w. - DOI - PubMed
    2. Minville J. Girardin M. Spino C. Can. J. Chem. 2007;85:603. doi: 10.1139/v07-091. - DOI
    3. Morita N. Krause N. Angew. Chem., Int. Ed. 2006;45:1897. doi: 10.1002/anie.200503846. - DOI - PubMed
    4. Krause N. Belting V. Deutsch C. Erdsack J. Fan H.-T. Gockel H. B. Hoffmann-Röder A. Morita N. Volz F. Pure Appl. Chem. 2008;80:1063.
    5. Tang J. Xu D.-Q. Xia A.-B. Wang Y.-F. Jiang J.-R. Luo S.-P. Xu X.-Y. Adv. Synth. Catal. 2010;352:2121. doi: 10.1002/adsc.201000245. - DOI
    6. Xiang Y. Song J. Zhang Y. Yang Y. D.-C. Guan Z. He Y.-H. J. Org. Chem. 2016;81:6042. doi: 10.1021/acs.joc.6b01132. - DOI - PubMed
    1. Newman D. J. Cragg G. M. J. Nat. Prod. 2016;79:629. doi: 10.1021/acs.jnatprod.5b01055. - DOI - PubMed
    1. Ding H. X. Leverett C. A. Kyne R. E. Liu K.-C. K. Fink S. J. Flick A. C. O'Donnell C. J. Bioorg. Med. Chem. 2015;23:1895. doi: 10.1016/j.bmc.2015.02.056. - DOI - PubMed
    2. Stockdale T. P. Williams C. M. Chem. Soc. Rev. 2015;44:7737. doi: 10.1039/C4CS00477A. - DOI - PubMed