Tertiary-Amine-Catalyzed Asymmetric [3+2] Annulations of Morita–Baylis–Hillman Carbonates of Isatins with Nitroolefins to Construct Spirooxindoles

Abstract

An enantioselective [3+2] annulation of nitroolefins with racemic Morita–Baylis–Hillman carbonates of isatins catalyzed by α-isocupreine has been developed. Chiral spirocyclic 2-oxindoles bearing an unusual cyclopentadiene motif were produced in excellent enantioselectivity (up to 98% ee) after the tandem elimination of HNO₂ in the presence of DIPEA.

Key words

Morita–Baylis–Hillman carbonates - asymmetric [3+2] annulation - spirooxindole - cyclopentadiene

• References

• 1a Bond RF, Boeyens JC. A, Holzapfel CW, Steyn PS. J. Chem. Soc., Perkin Trans. 1 1979; 1751
• 1b Greshock TJ, Grubbs AW, Jiao P, Wicklow DT, Gloer JB, Williams RM. Angew. Chem. Int. Ed. 2008; 47: 3573
• 1c Fensome A, Adams WR, Adams AL, Berrodin TJ, Cohen J, Huselton C, Illenberger A, Kern JC, Hudak VA, Marella MA, Melenski EG, McComas CC, Mugford CA, Slayden OD, Yudt M, Zhang Z, Zhang P, Zhu Y, Winneker RC, Wrobel JE. J. Med. Chem. 2008; 51: 1861
• 1d Mohr JT, Krout MR, Stoltz BM. Nature 2008; 455: 323
• 1e Miller KA, Tsukamoto S, Williams RM. Nat. Chem. 2009; 1: 63

For selected reviews, see:
• 2a Marti C, Carreira EM. Eur. J. Org. Chem. 2003; 2209
• 2b Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
• 2c Trost BM, Brennan MK. Synthesis 2009; 3003
• 2d Zhou F, Liu Y, Zhou J. Adv. Synth. Catal. 2010; 352: 1381
• 2e Hong L, Wang R. Adv. Synth. Catal. 2013; 355: 1023
• 2f Cheng D, Ishihara Y, Tan B, Barbas III CF. ACS Catal. 2014; 4: 743

For selected examples, see:
• 3a Sebahar PR, Williams RM. J. Am. Chem. Soc. 2000; 122: 5666
• 3b Chen X.-H, Wei Q, Luo S.-W, Xiao H, Gong L.-Z. J. Am. Chem. Soc. 2009; 131: 13819
• 3c Onishi T, Sebahar PR, Williams RM. Org. Lett. 2003; 5: 3135
• 3d Lv H, Tiwari B, Mo J, Xing C, Chi YR. Org. Lett. 2012; 14: 5412
• 3e Wang L.-L, Bai J.-F, Peng L, Qi L.-W, Jia L.-N, Guo Y.-L, Luo X.-Y, Xu X.-Y, Wang L.-X. Chem. Commun. 2012; 48: 5175
• 3f Wang L, Shi X.-M, Dong W.-P, Zhu L.-P, Wang R. Chem. Commun. 2013; 49: 3458

For selected examples, see:
• 4a Hanhan NV, Ball-Jones NR, Tran NT, Franz AK. Angew. Chem. Int. Ed. 2012; 51: 989
• 4b Dugal-Tessier J, O’Bryan EA, Schroeder TB. H, Cohen DT, Scheidt KA. Angew. Chem. Int. Ed. 2012; 51: 4963
• 4c Duan S.-W, Li Y, Liu Y.-Y, Zou Y.-Q, Shi D.-Q, Xiao W.-J. Chem. Commun. 2012; 48: 5160
• 4d Jiang X, Cao Y, Wang Y, Liu L, Shen F, Wang R. J. Am. Chem. Soc. 2010; 132: 15328
• 4e Wang X.-N, Zhang Y.-Y, Ye S. Adv. Synth. Catal. 2010; 352: 1892
• 4f Jiang K, Jia Z.-J, Yin X, Wu L, Chen Y.-C. Org. Lett. 2010; 12: 2766
• 4g Jia Z.-J, Jiang H, Li J.-L, Gschwend B, Li Q.-Z, Yin X, Grouleff J, Chen Y.-C, Jørgensen KA. J. Am. Chem. Soc. 2011; 133: 5053
• 4h Shen L.-T, Jia W.-Q, Ye S. Angew. Chem. Int. Ed. 2013; 52: 585
• 4i Manoni F, Connon SJ. Angew. Chem. Int. Ed. 2014; 53: 2628
• 4j Yin X.-P, Zeng X.-P, Liu Y.-L, Liao F.-M, Yu J.-S, Zhou F, Zhou J. Angew. Chem. Int. Ed. 2014; 53: 13740
• 5a Yamazaki M, Okuyama E, Kobayashi M, Inoue H. Tetrahedron Lett. 1981; 22: 135
• 5b Ondeyka JG, Goegelman RT, Schaeffer JM, Kelemen L, Zitano L. J. Antibiot. 1990; 43: 1375
• 5c Liesch JM, Wichmann CF. J. Antibiot. 1990; 43: 1380
• 5d Blanchflower SE, Banks RM, Everett JR, Manger BR, Reading C. J. Antibiot. 1991; 44: 492
• 5e Blanchflower SE, Banks RM, Everett JR, Reading C. J. Antibiot. 1993; 46: 1355
• 5f Banks RM, Blanchflower SE, Everett JR, Manger BR, Reading C. J. Antibiot. 1997; 50: 840
• 6a Tsuda M, Kasai Y, Komatsu K, Sone T, Tanaka M, Mikami Y, Kobayashi J. Org. Lett. 2004; 6: 3087
• 6b Mugishima T, Tsuda M, Kasai Y, Ishiyama H, Fukushi E, Kawabata J, Watanabe M, Akao K, Kobayashi J. J. Org. Chem. 2005; 70: 9430

For selected examples, see:
• 7a Trost BM, Cramer N, Silverman SM. J. Am. Chem. Soc. 2007; 129: 12396
• 7b Voituriez A, Pinto N, Neel M, Retailleau P, Marinetti A. Chem. Eur. J. 2010; 16: 12541
• 7c Albertshofer K, Anderson KE, Barbas III CF. Org. Lett. 2012; 14: 5968
• 7d Li X, Li Y.-M, Peng F.-Z, Wu S.-T, Li Z.-Q, Sun Z.-W, Zhang H.-B, Shao Z.-H. Org. Lett. 2011; 13: 6160
• 7e Li Y.-M, Li X, Peng F.-Z, Li Z.-Q, Wu S.-T, Sun Z.-W, Zhang H.-B, Shao Z.-H. Org. Lett. 2011; 13: 6200
• 7f Sun W, Zhu G, Wu C, Hong L, Wang R. Chem. Eur. J. 2012; 18: 6737

For reviews, see:
• 8a Liu T.-Y, Xie M, Chen Y.-C. Chem. Soc. Rev. 2012; 41: 4101
• 8b Wei Y, Shi M. Chem. Rev. 2013; 113: 6659

For selected examples, see:
• 8c Du Y, Lu X, Zhang C. Angew. Chem. Int. Ed. 2003; 42: 1035
• 8d 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
• 8e Deng H.-P, Wei Y, Shi M. Adv. Synth. Catal. 2012; 354: 783
• 8f Deng H.-P, Wei Y, Shi M. Org. Lett. 2011; 13: 3348
• 8g Hu F.-L, Wei Y, Shi M. Chem. Commun. 2014; 50: 8912
• 9a Zhong F, Han X, Wang Y, Lu Y. Angew. Chem. Int. Ed. 2011; 50: 7837
• 9b Tan B, Candeias NR, Barbas III CF. J. Am. Chem. Soc. 2011; 133: 4672
• 10a Iwabuchi Y, Nakatani M, Hatakeyama S. J. Am. Chem. Soc. 1999; 121: 10219
• 10b Waldmann H, Khedkar V, Dückert H, Schürmann M, Oppel IM, Kumar K. Angew. Chem. Int. Ed. 2008; 47: 6869
• 11 Peng J, Huang X, Jiang L, Cui H.-L, Chen Y.-C. Org. Lett. 2011; 13: 4584
• 12a Wang Y, Liu L, Zhang T, Zhong N.-J, Wang D, Chen Y.-J. J. Org. Chem. 2012; 77: 4143
• 12b Liu Y.-L, Wang X, Zhao Y.-L, Zhu F, Zeng X.-P, Chen L, Wang C.-H, Zhao X.-L, Zhou J. Angew. Chem. Int. Ed. 2013; 52: 13735
• 12c Zhong N.-J, Wei F, Xuan Q.-Q, Liu L, Wang D, Chen Y.-J. Chem. Commun. 2013; 49: 11071
• 12d Wei F, Huang H.-Y, Zhong N.-J, Gu C.-L, Wang D, Liu L. Org. Lett. 2015; 17: 1688
• 13 Zhou R, Duan C, Yang C, He Z. Chem. Asian J. 2014; 9: 1183
• 14 Belmessieri D, Morrill LC, Simal C, Slawin AM. Z, Smith AD. J. Am. Chem. Soc. 2011; 133: 2714
• 15 Nakamoto Y, Urabe F, Takahashi K, Ishihara J, Hatakeyama S. Chem. Eur. J. 2013; 19: 12653
• 16 Stephens PJ, Harada N. Chirality 2010; 22: 229