Asymmetric Synthesis of Novel Fused Polycyclic 3,4-Dihydro-pyrano[4,3-b]pyran-5(2H)-ones via an Organocatalyzed Formal[3+3] Annulation

doi:10.6023/cjoc201703070

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (8): 2203-2210.DOI: 10.6023/cjoc201703070 Previous Articles Next Articles

Special Issue: 陈茹玉先生诞辰100周年

Articles

有机催化不对称[3+3]环化合成新型光学活性稠合多环3,4-二氢吡喃并[4,3-b]吡喃-5-(2H)-酮

肖园园, 王有名, 周正洪

南开大学化学学院元素有机化学国家重点实验室天津 300071

收稿日期:2019-03-29 修回日期:2019-05-10 发布日期:2019-05-28
通讯作者: 周正洪 E-mail:z.h.zhou@nankai.edu.cn

Asymmetric Synthesis of Novel Fused Polycyclic 3,4-Dihydro-pyrano[4,3-b]pyran-5(2H)-ones via an Organocatalyzed Formal[3+3] Annulation

Xiao Yuanyuan, Wang Youming, Zhou Zhenghong

Institute and State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071

Received:2019-03-29 Revised:2019-05-10 Published:2019-05-28
Contact: 10.6023/cjoc201703070 E-mail:z.h.zhou@nankai.edu.cn

1. Asymmetric Synthesis of Novel Fused Polycyclic 3,4-Dihydro-pyrano[4,3-b]pyran-5(2H)-ones via an Organocatalyzed Formal[3+3] Annulation.PDF(6707KB)

Abstract

A chiral bifunctional squaramide catalyzed enantioselective formal[3+3] annulation of 4-hydroxy-2H-pyrano[2',3':4,5]pyrano[2,3-c]pyrazole-2,5(7H)-diones and (E)-2-nitroallyl acetates has been developed, which provides an efficient approach to stereocontrolled construction of fused polycyclic 3,4-dihydropyrano[4,3-b]pyran-5(2H)-one scaffold. Under the catalysis of a bifunctional squaramide derived from (1R,2R)-1,2-diphenylethane-1,2-diamine, a wide range of novel fused polycyclic 3,4-dihydropyrano[4,3-b]pyran-5(2H)-one derivatives with two adjacent stereogenic centers are obtained in acceptable yields with high anti-selectivity and moderate to excellent enantioselectivity. Representative transformation of the annulation product to other synthetic valuable compound is achieved without any loss of stereochemical integrity.

Key words: asymmetric synthesis, fused polycyclic 3,4-dihydropyrano[4,3-b]pyran-5(2H)-one, 4-hydroxy-2H-pyrano[2',3':4,5]pyrano[2,3-c]pyrazole-2,5(7H)-dione, (E)-2-nitroallyl acetate, organocatalysis

Cite this article

Xiao Yuanyuan, Wang Youming, Zhou Zhenghong. Asymmetric Synthesis of Novel Fused Polycyclic 3,4-Dihydro-pyrano[4,3-b]pyran-5(2H)-ones via an Organocatalyzed Formal[3+3] Annulation[J]. Chin. J. Org. Chem., 2019, 39(8): 2203-2210.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Liu, Y.; Zhang, X.; Zhan, Y.; Li, B.; Lu, W.; Nan, F. Tetrahedron 2019, 75, 1819.
(b) Zhan, Y.; Zhang, X.-W.; Xiong, Y.; Li, B.-L.; Nan, F.-J. Org. Biomol. Chem. 2016, 14, 747.
(c) Ohshiro, T.; Ohtawa, M.; Nagamitsu, T.; Matsuda, D.; Yagyu, H.; Davis, M. A.; Rudel, L. L.; Ishibashi, S.; Tomoda, H. J. Pharmacol. Exp. Ther. 2015, 355, 297.
(d) Nong, X.-H.; Wang, Y.-F.; Zhang, X.-Y.; Zhou, M.-P.; Xu, X.-Y.; Qi, S.-H. Mar. Drugs 2014, 12, 6113.
(e) Ohtawa, M.; Yamazaki, H.; Matsuda, D.; Ohshiro, T.; Rudel, L. L.; Tomoda, S. H.; Nagamitsu, T. Bioorg. Med. Chem. Lett. 2013, 23, 2659.
(f) Jiang, X.; Ao, L.; Zhou, C.; Yang, L.; Zhang, Q.; Li, H.; Sun, L.; Wu, X.; Bai, H.; Zhao, Y. Chem. Biodiversity 2005, 2, 557.
(g) Handa, M.; Sunazuka, T.; Nagai, K.; Kimura, R.; Shirahata, T.; Tian, Z.-M.; Otoguro, K.; Harigaya, Y.; ōmura, S. J. Antibiot. 2001, 54, 382.
(h) Otogwo, K.; Kuno, F.; ōmura, S. Pharmacol. Ther. 1997, 76, 45.
(i) Kuno, F.; Otoguro, K.; Shiomi, K.; Iwai, Y.; ōmura, S. J. Antibiot. 1996, 49, 742.
(j) Tomoda, H.; Kim, Y. K.; Nishida, H.; Masuma, R.; ōmura, S. J. Antibiot. 1994, 47, 148.
[2] Kumar, R.; Yadav, N.; Lavilla, R.; Blasi, D.; Quintana, J.; Brea, J. M.; Loza, M. I.; Mestres, J.; Bhandari, M.; Arora, R.; Kakkar, R.; Prasad, A. K. Mol. Diversity 2017, 21, 533.
[3] Huang, L.-J.; Hour, M.-J.; Teng, C.-M.; Kuo, S.-C. Chem. Pharm. Bull. 1992, 40, 2547.
[4] Kuo, S.-C.; Huang, L.-J.; Nakamura, H. J. Med. Chem. 1984, 27, 539.
[5] (a) Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G.-Q.; Barluenga, S.; Mitchell, H. J. J. Am. Chem. Soc. 2000, 122, 9939.
(b) Garcia-Castro, M.; Zimmermann, S.; Sankar, M. G.; Kumar, K. Angew. Chem., Int. Ed. 2016, 55, 7586.
[6] (a) Liu, J.-Y.; Yang, X.-C.; Lu, H.; Gu, Y.-C.; Xu, P.-F. Org. Lett. 2018, 20, 2190.
(b) Basu, P.; Sikdar, R.; Kumar, T.; Namboothiri, I. N. N. Eur. J. Org. Chem. 2018, 5735.
(c) Zhang, J.; Yin, G.; Du, Y.; Yang, Z.; Li, Y.; Chen, L. J. Org. Chem. 2017, 82, 13594.
(d) Zheng, Y.; Cui, L.; Wang, Y.; Zhou, Z. J. Org. Chem. 2016, 81, 4340.
(e) Xie, J.; Sha, F.; Wu, X.-Y. Tetrahedron 2016, 72, 4047.
(f) Nair, D. K.; Menna-Barreto, R. F. S.; da Silva Júnior, E. N.; Mobind, S. M.; Namboothiri, I. N. N. Chem. Commun. 2014, 50, 6973.
[7] CCDC-1894281 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

[1]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[2]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[3]	Chun-Xia Cheng, Lu-Ping Wu, Feng Sha, Xin-Yan Wu. Enantioselective Vinylogous Allylic Alkylation of Coumarins with Morita-Baylis-Hillman Carbonates Catalyzed by Chiral Phosphine-Amide [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3188-3195.
[4]	Yuchao Wang, Jinbiao Liu, Zhitao He. Palladium-Catalyzed Asymmetric Hydrofunctionalizations of Conjugated Dienes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2614-2627.
[5]	Yiwen Quan, Xinhui Jiang, Wenjun Li, Jian Wang. Access to α-Vinyl β-Alkynyl Enals via an Organocatalytic Deconjugation-Aldol Condensation Sequence [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2120-2125.
[6]	Tingyu Song, Ran Li, Lihua Huang, Shikun Jia, Guangjian Mei. Catalytic Asymmetric Synthesis of N—N Atropisomers [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1977-1990.
[7]	Cheng Luo, Yanli Yin, Zhiyong Jiang. Recent Advances in Asymmetric Synthesis of P-Chiral Phosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1963-1976.
[8]	Ke Jing, Panke Zhang, Senmiao Xu. Application of 1,4-Azaborines in Organic and Transition Metal Catalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1742-1750.
[9]	Xinyu Zhang, Huihui Geng, Shilei Zhang, Wei Wang, Xiaobei Chen. A Method for the Synthesis of Deuterated Benzoins Catalyzed by N-Heterocyclic Carbene [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1510-1516.
[10]	Weidi Cao, Xiaohua Liu. Recent Advances on Catalytic Enantioselective Protonation for Construction of α-Tertiary Carbonyl Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 961-973.
[11]	Ling Meng, Jun Wang. Research Progress on Synthesis of Thioflavonoids [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 873-891.
[12]	Chunbo Dai, Siqi Xia, Xiaoyu Chen, Limin Yang. N-Heterocyclic Carbene (NHC)-Catalyzed [4+3] Cycloaddition to Synthesize 4-Aminobenzoheptenolactons [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1084-1090.
[13]	Huaiyuan Zhang, Nuo Xu, Rongping Tang, Xingli Shi. Recent Advances in Asymmetric Dearomatization Reactions Induced by Chiral Hypervalent Iodine Reagents [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3784-3805.
[14]	Yushan Zhang, Zhen Huan, Jindong Yang, Jinpei Cheng. Recent Advances in Hydrogen Transfer Reactivities of N-Heterocyclic Phosphines [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3806-3825.
[15]	Liu-Yang Pu, Zhiyue Li, Limin Li, Yucui Ma, Min Ma, Shengquan Hu, Zhengzhi Wu. Asymmetric Synthesis of (–)-Colchicine and Its Natural Analog (–)-N-Acetylcolchicine Methyl Ether [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 313-319.

有机催化不对称[3+3]环化合成新型光学活性稠合多环3,4-二氢吡喃并[4,3-b]吡喃-5-(2H)-酮

Asymmetric Synthesis of Novel Fused Polycyclic 3,4-Dihydro-pyrano[4,3-b]pyran-5(2H)-ones via an Organocatalyzed Formal[3+3] Annulation

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments