Asymmetric [3+2] Cycloaddition of Olefins with Morita–Baylis–Hillman Carbonates Catalyzed by BINOL-Based Bifunctional Phosphine

Abstract

We have developed a series of novel BINOL-based phosphines. These bifunctional organocatalysts can be used in the [3+2] cycloaddition of electron-deficient olefins and Morita–Baylis–Hillman (MBH) carbonates. Moderate to excellent yields (up to >99%) and good to excellent enantioselectivities (up to 95% ee) can be obtained in the cycloaddition reaction of maleimides and MBH carbonates. The application of these novel phosphines can be further extended to the asymmetric synthesis of chiral spirooxindoles (up to 85% ee). The results in this study indicate that the BINOL moiety plays an important role in stereocontrol.

Key words

BINOL - phosphine - organocatalyst - Morita–Baylis–Hillman derivative - cycloaddition

• References and Notes


For reviews on phosphine catalysts, see:
• 1a Ni H, Chan W.-L, Lu Y. Chem. Rev. 2018; 118: 9344
• 1b Guo H, Fan YC, Sun Z, Wu Y, Kwon O. Chem. Rev. 2018; 118: 10049
• 1c Fan YC, Kwon O. Chem. Commun. 2013; 11588
• 1d Li W, Zhang J. Chem. Soc. Rev. 2016; 45: 1657
• 1e Wang T, Han X, Zhong F, Yao W, Lu Y. Acc. Chem. Res. 2016; 49: 1369
• 1f Wei Y, Shi M. Acc. Chem. Res. 2010; 43: 1005
• 1g Methot JL, Roush WR. Adv. Synth. Catal. 2004; 346: 1035
• 1h Wang Z, Xu X, Kwon O. Chem. Soc. Rev. 2014; 43: 2927
• 1i Xiao Y, Sun Z, Guo H, Kwon O. Beilstein J. Org. Chem. 2014; 10: 2089
• 1j Xiao Y, Guo H, Kwon O. Aldrichimica Acta 2016; 49: 3

For reviews on bifunctional catalysis, see:
• 2a Paull DH, Abraham CJ, Scerba MT, Alden-Danforth E, Lectka T. Acc. Chem. Res. 2008; 41: 655
• 2b Matsunaga S, Shibasaki M. Chem. Commun. 2014; 1044
• 3a Shi M, Chen L.-H, Li C.-Q. J. Am. Chem. Soc. 2005; 127: 3790
• 3b Hu F.-L, Wei Y, Shi M. Chem. Commun. 2014; 8912
• 3c Shi M, Chen L.-H. Chem. Commun. 2003; 1310
• 3d Liu Y.-H, Chen L.-H, Shi M. Adv. Synth. Catal. 2006; 348: 973
• 3e Zhang X.-N, Shi M. Eur. J. Org. Chem. 2012; 6271
• 3f Matsui K, Takizawa S, Sasai H. Synlett 2006; 761
• 3g Ito K, Nishida K, Gotanda T. Tetrahedron Lett. 2007; 48: 6147
• 4 Cowen BJ, Miller SC. J. Am. Chem. Soc. 2007; 129: 10988
• 5 Fang Y.-Q, Jacobsen EN. J. Am. Chem. Soc. 2008; 130: 5660
• 6a Xiao H, Chai Z, Zheng C.-W, Yang Y.-Q, Liu W, Zhang J.-K, Zhao G. Angew. Chem. Int. Ed. 2010; 49: 4467
• 6b Lou Y.-P, Zheng C.-W, Pan R.-M, Jin Q.-W, Zhao G, Li Z. Org. Lett. 2015; 17: 688
• 6c Zhang J, Cao D, Wang H, Zheng C, Zhao G, Shang Y. J. Org. Chem. 2016; 81: 10558
• 7a Zhong F, Han X, Wang Y, Lu Y. Angew. Chem. Int. Ed. 2011; 50: 7837
• 7b Ni H, Yu Z, Yao W, Lan Y, Ullah N, Lu Y. Chem. Sci. 2017; 8: 5699
• 7c Han X, Wang Y, Zhong F, Lu Y. J. Am. Chem. Soc. 2011; 133: 1726
• 7d Zhong F, Wang Y, Han X, Huang K.-W, Lu Y. Org. Lett. 2011; 13: 1310
• 7e Han X, Wang S.-X, Zhong F, Lu Y. Synthesis 2011; 1859
• 7f Han X, Wang Y, Zhong F, Lu Y. Org. Biomol. Chem. 2011; 9: 6734
• 8a Wang H, Lu W, Zhang J. Chem. Eur. J. 2017; 23: 13587
• 8b Zhang J, Wu H.-H, Zhang J. Org. Lett. 2017; 19: 6080
• 8c Chen P, Zhang J. Org. Lett. 2017; 19: 6550
• 8d Huang B, Li C, Wang H, Wang C, Liu L, Zhang J. Org. Lett. 2017; 19: 5102

For the development of novel chiral phosphine catalysts from other groups, see:
• 9a Henry CE, Xu Q, Fan YC, Martin TJ, Belding L, Dudding T, Kwon O. J. Am. Chem. Soc. 2014; 136: 11890
• 9b Voituriez A, Panossian A, Fleury-Brégeot N, Retailleaua P, Marinetti A. J. Am. Chem. Soc. 2008; 130: 14030
• 9c Su HY, Taylor MS. J. Org. Chem. 2017; 82: 3173
• 9d Jin H, Zhang Q, Li E, Jia P, Li N, Huang Y. Org. Biomol. Chem. 2017; 15: 7079
• 9e Kitagaki S, Nakamura K, Kawabata C, Ishikawa A, Takenaga N, Yoshida K. Org. Biomol. Chem. 2018; 16: 1770
• 9f Li H, Luo J, Li B, Yi X, He Z. Org. Lett. 2017; 19: 5637
• 9g Qin C, Liu Y, Yu Y, Fu Y, Li H, Wang W. Org. Lett. 2018; 20: 1304
• 9h Wang C, Gao Z, Zhou L, Wang Q, Wu Y, Yuan C, Liao J, Xiao Y, Guo H. Chem. Commun. 2018; 279
• 9i Isenehher PG, Bächle F, Pfaltz A. Chem. Eur. J. 2016; 22: 17595
• 9j Kang T.-C, Wu L.-P, Yu Q.-W, Wu X.-Y. Chem. Eur. J. 2017; 23: 6509
• 9k Lee SY, Fujiwara Y, Nishiguchi A, Kalek M, Fu GC. J. Am. Chem. Soc. 2015; 137: 4587
• 9l Wang Q.-G, Zhu S.-F, Ye L.-W, Zhou C.-Y, Sun X.-L, Tang Y, Zhou Q.-L. Adv. Synth. Catal. 2010; 352: 1914
• 9m Zhou L, Yuan C, Zeng Y, Liu H, Wang C, Gao X, Wang Q, Zhang C, Guo H. Chem. Sci. 2018; 9: 1831
• 9n Gicquel M, Zhang Y, Aillard P, Retailleau P, Voituriez A, Marinetti A. Angew. Chem. Int. Ed. 2015; 54: 5470
• 9o Smith SW, Fu GC. J. Am. Chem. Soc. 2009; 131: 14231
• 9p Li E, Jin H, Jia P, Dong X, Huang Y. Angew. Chem. Int. Ed. 2016; 55: 11591
• 10a Zhong F, Chen G.-Y, Han X, Yao W, Lu Y. Org. Lett. 2012; 14: 3764
• 10b Deng H.-P, Wang D, Wei Y, Shi M. Beilstein J. Org. Chem. 2012; 8: 1098
• 10c Hu H, Yu S, Zhu L, Zhou L, Zhong W. Org. Biomol. Chem. 2016; 14: 752

For reviews on transformations of Morita–Baylis–Hillman carbonates, see:
• 11a Liu T.-Y, Xie M, Chen Y.-C. Chem. Soc. Rev. 2012; 41: 4101
• 11b Xie P, Huang Y. Org. Biomol. Chem. 2015; 13: 8578
• 11c Singh V, Batra S. Tetrahedron 2008; 64: 4511
• 11d Basavaiah D, Reddy BS, Badsara SS. Chem. Rev. 2010; 110: 5447
• 11e Wei Y, Shi M. Chem. Rev. 2013; 113: 6659
• 11f Basavaiah D, Veeraraghavaiah G. Chem. Soc. Rev. 2012; 41: 68
• 11g Zhou R, He Z. Eur. J. Org. Chem. 2016; 1937

For studies on transformations of MBH derivatives from our group, see:
• 12a Liu S.-W, Gao Y.-J, Shi Y, Zhou L, Tang X, Cui H.-L. J. Org. Chem. 2018; 83: 13754
• 12b Tang X, Gao Y.-J, Deng H.-Q, Lei J.-J, Liu S.-W, Zhou L, Shi Y, Liang H, Qiao J, Guo L, Han B, Cui H.-L. Org. Biomol. Chem. 2018; 16: 3362
• 12c Tang X, Yang M.-C, Ye C, Liu L, Zhou H.-L, Jiang X.-J, You X.-L, Han B, Cui H.-L. Org. Chem. Front. 2017; 4: 2128
• 13a Deng H.-P, Wei Y, Shi M. Org. Lett. 2011; 13: 3348
• 13b Tan B, Candeias NR, Barbas CF. III. J. Am. Chem. Soc. 2011; 133: 4672
• 14 For detailed optimization results, see the Supporting Information