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. 2019 Apr 12;9(20):11585-11588.
doi: 10.1039/c9ra00155g. eCollection 2019 Apr 9.

Asymmetric synthesis of multifunctional aryl allyl ethers by nucleophilic catalysis

Shuai Zhao  1 , Lei Jin  1 , Zhi-Li Chen  1 , Xue Rui  1 , Jia-Yi He  1 , Ran Xia  1 , Ke Chen  1 , Xiang-Xiang Chen  1 , Zi-Jian Yin  1 , Xin Chen  1
Affiliations

Asymmetric synthesis of multifunctional aryl allyl ethers by nucleophilic catalysis

Shuai Zhao et al. RSC Adv. .

Abstract

Asymmetric allylic substitution of Morita-Baylis-Hillman (MBH) carbonates with less-nucleophilic phenols mediated by nucleophilic amine catalysis was successfully developed. A variety of substituted aryl allyl ethers were afforded with moderate to high yields with excellent enantioselectivities. The chiral MBH alcohol could be easily accessed from the corresponding aryl allyl ether.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Chiral nucleophilic catalysts screened.
Scheme 1
Scheme 1. (a) Synthesis of aryl allyl ether 4a from MBH carbonate 5a by nucleophilic catalysis. (b) Synthesis of chiral MBH alcohol 6. (c) 1,3-dipolar cycloaddition reaction of aryl allyl ether 4a and chlorobenzaldoxime.
Scheme 2
Scheme 2. Proposed mechanism of the asymmetric allylic substitution reaction.
See this image and copyright information in PMC

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References

    1. For selected reviews, see:

    2. Huang W.-Y. Anwar S. Chen K. Chem. Rec. 2017;17:1. doi: 10.1002/tcr.201600075. - DOI - PubMed
    3. Basavaiah D. Reddy B. S. Badsara S. S. Chem. Rev. 2010;110:5447. doi: 10.1021/cr900291g. - DOI - PubMed
    4. Xie P. Huang Y. Org. Biomol. Chem. 2015;13:8578. doi: 10.1039/C5OB00865D. - DOI - PubMed
    5. Bharadwaj K. C. RSC Adv. 2015;5:75923. doi: 10.1039/C5RA13611C. - DOI

    1. For selected reviews, see:

    2. Rios R. Catal. Sci. Technol. 2012;2:267. doi: 10.1039/C1CY00387A. - DOI
    3. Fan Y. C. Kwon O. Chem. Commun. 2013;49:11588. doi: 10.1039/C3CC47368F. - DOI - PMC - PubMed
    4. Liu T.-Y. Xie M. Chen Y.-C. Chem. Soc. Rev. 2012;41:4101. doi: 10.1039/C2CS35017C. - DOI - PubMed
    5. Wei Y. Shi M. Chem. Rev. 2013;113:6659. doi: 10.1021/cr300192h. - DOI - PubMed
    6. Pellissier H. Tetrahedron. 2017;73:2831. doi: 10.1016/j.tet.2017.04.008. - DOI

    1. For selected examples, see:

    2. Wang X. Wang X. Han Z. Wang Z. Ding K. Angew. Chem., Int. Ed. 2017;56:1116. doi: 10.1002/anie.201609332. - DOI - PubMed
    3. Liu J. Han Z. Wang X. Meng F. Wang Z. Ding K. Angew. Chem., Int. Ed. 2017;56:5050. doi: 10.1002/anie.201701455. - DOI - PubMed
    4. Zhu Y. Mao Y. Mei H. Pan Y. Han J. Soloshonok V. A. Hayashi T. Chem.–Eur. J. 2018;24:8994. doi: 10.1002/chem.201801670. - DOI - PubMed
    5. Wang X. Guo P. Han Z. Wang X. Wang Z. Ding K. J. Am. Chem. Soc. 2014;136:405. doi: 10.1021/ja410707q. - DOI - PubMed
    6. Gowrisankar S. Lee H. S. Kim S. H. Lee K. Y. Kim J. N. Tetrahedron. 2009;65:8769. doi: 10.1016/j.tet.2009.07.034. - DOI
    1. Basavaiah D. Rao A. J. Satyanarayana T. Chem. Rev. 2003;103:811. doi: 10.1021/cr010043d. - DOI - PubMed
    2. Basavaiah D. Rao K. V. Reddy R. J. Chem. Soc. Rev. 2007;36:1581. doi: 10.1039/B613741P. - DOI - PubMed
    3. Singh V. Batra S. Tetrahedron. 2008;64:4511. doi: 10.1016/j.tet.2008.02.087. - DOI
    1. Junior C. G. L. Vasconcellos M. L. A. A. Bioorg. Med. Chem. 2012;20:3954. doi: 10.1016/j.bmc.2012.04.061. - DOI - PubMed
    2. Yu C.-R. Xu L.-H. Tu S. Li Z.-N. Li B. J. Fluorine Chem. 2006;127:1540. doi: 10.1016/j.jfluchem.2006.07.011. - DOI
    3. Cocco M. Pellegrini C. Martínez-Banaclocha H. Giorgis M. Marini E. Costale A. Miglio G. Fornai M. Antonioli L. López-Castejón G. Tapia-Abellán A. Angosto D. Hafner-Bratkovič I. Regazzoni L. Blandizzi C. Pelegrín P. Bertinaria M. J. Med. Chem. 2017;60:3656. doi: 10.1021/acs.jmedchem.6b01624. - DOI - PubMed