Chinese Journal of Organic Chemistry >
Phosphine-Catalyzed[3+2] Annulations with γ-Methyl Allenoates
Received date: 2019-01-25
Revised date: 2019-03-22
Online published: 2019-04-09
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21702189, 21672193, 21272218), the China Postdoctoral Science Foundation (Nos. 2017M610458, 2018T110737) and the Postdoctoral Research Grant in Henan Province (No. 001701006).
The phosphine-catalyzed[3+2] annulation of γ-methyl allenoates with 2-arylidene-1H-indene-1,3(2H)-diones is reported. In the reaction, a series of highly functionalized spiro[4.4]dec-6-ene skeletons were obtained in moderate to good yields and high diastereoselectivities. It should be noted that the perfect α-regioselective annulation adducts were obtained with simple PPh3 catalyst.
Key words： phosphine-catalyzed; γ-methyl allenoates; [3+2]annulation
Ma Rong , Song Gege , Xi Qiuzhen , Yang Liu , Li Er-Qing , Duan Zheng . Phosphine-Catalyzed[3+2] Annulations with γ-Methyl Allenoates[J]. Chinese Journal of Organic Chemistry, 2019 , 39(8) : 2196 -2202 . DOI: 10.6023/cjoc201901040
[1] (a) Tan, B.; Candeias, N. R.; Barbas Ⅲ, C. F. Nat. Chem. 2011, 3, 473.
(b) Tan, B.; Candeias, N. R.; Barbas Ⅲ, C. F. J. Am. Chem. Soc. 2011, 133, 4672.
(c) Tan, B.; Hernandez-Torres, G.; Barbas Ⅲ, C. F. J. Am. Chem. Soc. 2011, 133, 12354.
(d) Cao, Y.; Jiang, X.; Liu, L.; Shen, F.; Zhang, F.; Wang, R. Angew. Chem., Int. Ed. 2011, 50, 9124.
(e) Zhong, F.; Han, X.; Wang, Y.; Lu, Y. Angew. Chem., Int. Ed. 2011, 50, 7837.
(f) Bencivenni, G.; Wu, L.-Y.; Mazzanti, A.; Giannichi, B.; Pesciaioli, F.; Song, M.-P.; Bartoli, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2009, 48, 7200.
[2] (a) Hojo, D.; Noguchi, K.; Tanaka, K. Angew. Chem., Int. Ed. 2009, 48, 8129.
(b) Tanaka, K.; Otake, Y.; Sagae, H.; Noguchi, K.; Hirano, M. Angew. Chem., Int. Ed. 2008, 47, 1312.
(c) Trost, B. M.; Cramer, N.; Silverman, S. M. J. Am. Chem. Soc. 2007, 129, 12396.
[3] (a) Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906.
(b) Lu, Z.; Zheng, S.; Zhang, X.; Lu, X. Org. Lett. 2008, 10, 3267.
(c) Zhang, B.; He, Z.; Xu, S.; Wu, G.; He, Z. Tetrahedron 2008, 64, 9471.
(d) Tian, J.; He, Z. Chem. Commun. 2013, 49, 2058.
[4] (a) Fan, Y. C.; Sun, Z.; Wu, Y.; Kwon, O. Chem. Rev. 2018, 118, 10049.
(b) Zhang, J.; Abudukeremu, M.; Miao, Z. Chin. J. Org. Chem. 2017, 37, 2859(in Chinese). (张甲勇,木尼热·阿布都克力木,苗志伟,有机化学, 2017, 37, 2859.)
(c) Xie, P.; Huang, Y. Org. Biomol. Chem. 2015, 13, 8578.
(d) Xu, S.; He, Z. Guo, H. Chin. J. Org. Chem. 2014, 34, 2438(in Chinese). (徐四龙,贺峥杰,有机化学, 2014, 34, 2438.)
(e) Wang, Z.; Xu, X.; Kwon, O. Chem. Soc. Rev. 2014, 43, 2927.
(e) Xu, S.; He, Z. Chin. J. Org. Chem. 2012, 32, 1159(in Chinese). (徐四龙,贺峥杰,有机化学, 2012, 32, 1159.)
(f) Ye, L.-W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140.
(g) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
[5] (a) Zhu, X.-F.; Lan, J.; Kwon, O. J. Am. Chem. Soc. 2003, 125, 4716.
(b) Tran, Y. S.; Kwon, O. J. Am. Chem. Soc. 2007, 129, 12632.
(c) Chen, R.; Fan, X.; Xu, Z.; He, Z. Chin. J. Chem. 2017, 35, 1469.
[6] Zhang, Q.; Yang, L.; Tong, X. J. Am. Chem. Soc. 2010, 132, 2550.
[7] (a) Xu, S.; Zhou, L.; Ma, R.; Song, H.; He, Z. Chem.-Eur. J. 2009, 15, 8698.
(b) Meng, X.; Huang, Y.; Zhao, H.; Xie, P.; Ma, J.; Chen, R. Org. Lett. 2009, 11, 991.
(c) Zhao, H.; Meng, X.; Huang, Y. Chem. Commun. 2013, 49, 10513.
(d) Li, E.; Jia, P.; Liang, L.; Huang, Y. ACS Catal. 2014, 4, 600.
(e) Li, E.; Chang, M.; Liang, L.; Huang, Y. Eur. J. Org. Chem. 2015, 710.
(f) Li, E.; Jin, H.; Huang, Y. ChemistrySelect 2018, 3, 12007.
[8] Zhang, X.-C.; Cao, S.-H.; Wei, Y.; Shi, M. Chem. Commun. 2011, 47, 1548.
[9] Gomez, C.; Gicquel, M.; Carry, J.-C.; Schio, L.; Retailleau, P.; Voituriez, A.; Marinetti, A. J. Org. Chem. 2013, 78, 1488.
[10] Li, E.; Huang, Y.; Liang, L.; Xie, P. Org. Lett. 2013, 15, 3138.
[11] CCDC 1579810 (3e) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
[12] (a) Liang, Y.; Liu, S.; Xia, Y.; Li, Y.; Yu, Z.-X. Chem.-Eur. J. 2008, 14, 4361.
(b) Mercier, E.; Fonovic, B.; Henry, C.; Kwon, O.; Dudding, T. Tetrahedron Lett. 2007, 48, 3617.
(c) Xia, Y.; Liang, Y.; Chen, Y.; Wang, M.; Jiao, L.; Huang, F.; Liu, S.; Li, Y.; Yu, Z.-X. J. Am. Chem. Soc. 2007, 129, 3470.
(d) Dudding, T.; Kwon, O.; Mercier, E. Org. Lett. 2006, 8, 3643.
(e) Zhu, X.-F.; Henry, C. E.; Kwon, O. J. Am. Chem. Soc. 2007, 129, 6722.
[13] Goswami, P.; Das, B. Tetrahedron Lett. 2009, 50, 897.
[14] Lang, R. W.; Hansen, H.-J. Org. Synth. 1990, 62, 202.
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