Synlett 2019; 30(12): 1474-1478
DOI: 10.1055/s-0037-1611860
letter
© Georg Thieme Verlag Stuttgart · New York

Catalytic Asymmetric Intramolecular Bromolactonization of α,β-Unsaturated Ketones

Shenghui Liu
a   International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education (MOE), College of Pharmacy, Jinan University, Guangzhou 510632, P. R. of China   eMail: chemjxj2015@jnu.edu.cn
,
Hailong He
b   Guangzhou Wanglaoji Pharmaceutical Company Limited, Guangzhou 510450, P. R. of China
,
Min Gan
a   International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education (MOE), College of Pharmacy, Jinan University, Guangzhou 510632, P. R. of China   eMail: chemjxj2015@jnu.edu.cn
,
Peng Yi
a   International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education (MOE), College of Pharmacy, Jinan University, Guangzhou 510632, P. R. of China   eMail: chemjxj2015@jnu.edu.cn
,
a   International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education (MOE), College of Pharmacy, Jinan University, Guangzhou 510632, P. R. of China   eMail: chemjxj2015@jnu.edu.cn
› Institutsangaben
We thank the Natural Science Foundation of Guangdong Province (Grant No. 2017B050506006) and Fundamental Research Funds for the Central University (Grant No. 21617470) for financial support.
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Publikationsverlauf

Received: 29. April 2019

Accepted after revision: 21. Mai 2019

Publikationsdatum:
12. Juni 2019 (online)


Abstract

Enantioselective bromolactonization by using an amino-urea catalyst to generate the important bromo-containing 3,4-dihydroisocoumarins is described. Excellent yields and good enantioselectivities could be achieved for various 3,4-dihydroisocoumarin compounds.

Supporting Information

 
  • References and Notes


    • For selected examples, see:
    • 1a Guimaràes KG, Souza Filho JD, Mares-Guia TR, Braga FG. Phytochemistry 2008; 69: 439
    • 1b Sun H, Ho CL, Ding F, Soehano I, Liu X.-W, Liang Z.-X. J. Am. Chem. Soc. 2012; 134: 11924
    • 1c Shimojima Y, Hayashi H, Ooka T, Shibukawa M, Iitaka Y. Tetrahedron 1984; 40: 2519
    • 1d Itoh J, Shomura T, Omoto S, Miyado S, Yuda Y, Shibata U, Inouye S. Agric. Biol. Chem. 1982; 46: 1255
    • 1e Van der Merwe KJ, Steyn PS, Fourie L, Scott DB, Theron JJ. Nature 1965; 205: 1112
    • 1f Malir F, Ostry V, Pfohlleszkowicz A, Malir J, Toman J. Toxins 2016; 8: 191
    • 1g Endringer DC, Guimaràes KG, Kondratyuk TP, Pezzuto JM, Braga FC. J. Nat. Prod. 2008; 71: 1082

      For selected examples, see:
    • 2a Islam MS, Ishigami K, Watanabe H. Tetrahedron 2007; 63: 1074
    • 2b Chakraborty TK, Chattopadhyay AK. J. Org. Chem. 2008; 73: 3578
    • 2c Habel A, Boland W. Org. Biomol. Chem. 2008; 6: 1601
    • 2d Feng Y, Jiang X, De Brabander JK. J. Am. Chem. Soc. 2012; 134: 17083
    • 3a Fujita M, Yoshida Y, Miyata K, Wakisaka A, Sugimura T. Angew. Chem. Int. Ed. 2010; 49: 7068
    • 3b Cornaggia C, Manoni F, Torrente E, Tallon S, Connon SJ. Org. Lett. 2012; 14: 1850
    • 3c Suzuki Y, Seki T, Tanaka S, Kitamura M. J. Am. Chem. Soc. 2015; 137: 9539
    • 3d Parhi B, Maity S, Ghorai P. Org. Lett. 2016; 18: 5220
    • 3e Woerly EM, Banik SM, Jacobsen EN. J. Am. Chem. Soc. 2016; 138: 13858
    • 3f Li W, Wiesenfeldt MP, Glorius F. J. Am. Chem. Soc. 2017; 139: 2585
    • 3g Chen J, Zhou L, Tan CK, Yeung Y.-Y. J. Org. Chem. 2012; 77: 999

      For selective reviews, see:
    • 4a Cheng YA, Yu WZ, Yeung Y.-Y. Org. Biomol. Chem. 2014; 12: 2333
    • 4b Tan CK, Yu WZ, Yeung Y.-Y. Chirality 2014; 26: 328
    • 4c Murai K, Fujioka H. Heterocycles 2013; 87: 763
    • 4d Tan CK, Yeung Y.-Y. Chem. Commun. 2013; 49: 7985
    • 4e Chemler SR, Bovino MT. ACS Catal. 2013; 3: 1076
    • 4f Denmark SE. Kuester W. E., Burk M. T. 2012; 51: 10938
    • 4g Hennecke U. Chem. Asian J. 2012; 7: 456
    • 4h Castellanos A, Fletcher SP. Chem. Eur. J. 2011; 17: 5766
    • 4i Tan CK, Zhou L, Yeung Y.-Y. Synlett 2011; 1335
    • 4j Zheng S, Schienebeck CM, Zhang W, Wang H.-Y, Tang W. Asian J. Org. Chem. 2014; 3: 366
    • 4k Sakakura A, Ishihara K. Chem. Rec. 2015; 15: 728

      Urea-catalyzed asymmetric halocyclizations:
    • 5a Veitch GE, Jacobsen EN. Angew. Chem. Int. Ed. 2010; 49: 7332
    • 5b Zhang W, Zheng S, Liu N, Werness JB, Guzei IA, Tang W. J. Am. Chem. Soc. 2010; 132: 3664
    • 5c Zheng S, Schienebeck CM, Zhang W, Wang H.-Y, Tang W. Asian J. Org. Chem. 2014; 3: 366
    • 5d Zhang W, Liu N, Schienebeck CM, Decloux K, Zheng S, Werness JB, Tang W. Chem. Eur. J. 2012; 18: 7296
    • 6a Denmark SE, Beutner GL. Angew. Chem. Int. Ed. 2008; 47: 1560
    • 6b Denmark SE, Burk MT. Proc. Natl. Acad. Sci. U.S.A. 2010; 107: 20655
    • 6c Denmark SE, Collins WR. Org. Lett. 2007; 9: 3801
    • 6d Denmark SE, Kalyani D, Collins WR. J. Am. Chem. Soc. 2010; 132: 15752
    • 6e Chen F, Tan CK, Yeung Y.-Y. J. Am. Chem. Soc. 2013; 135: 1232
    • 6f Ke Z, Tan CK, Chen F, Yeung Y.-Y. J. Am. Chem. Soc. 2014; 136: 5627
    • 6g Ke Z, Tan CK, Liu Y, Lee KG. Z, Yeung Y.-Y. Tetrahedron 2016; 72: 2683
    • 6h Cheng YA, Yu WZ, Yeung Y.-Y. Angew. Chem. Int. Ed. 2015; 54: 12102
    • 6i Jiang X, Tan CK, Zhou L, Yeung Y.-Y. Angew. Chem. Int. Ed. 2012; 51: 7771
    • 6j Tay DW, Leung GY. C, Yeung Y.-Y. Angew. Chem. Int. Ed. 2014; 53: 5161
    • 6k Zhao Y, Jiang X, Yeung Y.-Y. Angew. Chem. Int. Ed. 2013; 52: 8597
    • 6l Tan CK, Le C, Yeung Y.-Y. Chem. Commun. 2012; 48: 5793
    • 6m Tan CK, Zhou L, Yeung Y.-Y. Org. Lett. 2011; 13: 2738
    • 6n Zhou L, Tan CK, Jiang X, Chen F, Yeung Y.-Y. J. Am. Chem. Soc. 2010; 132: 15474
    • 6o Zhou L, Chen J, Tan CK, Yeung Y.-Y. J. Am. Chem. Soc. 2011; 133: 9164
    • 6p Chen J, Zhou L, Yeung Y.-Y. Org. Biomol. Chem. 2012; 10: 3808
    • 6q Zhou L, Tay DW, Chen J, Leung GY. C, Yeung Y.-Y. Chem. Commun. 2013; 49: 4412

      Selected recent endeavors on the development of asymmetric O-type halocyclization:
    • 7a Han X, Dong C, Zhou H.-B. Adv. Synth. Catal. 2014; 356: 1275
    • 7b Murai K, Nakajima J, Nakamura A, Hyogo N, Fujioka H. Chem. Asian J. 2014; 9: 3511
    • 7c Murai K, Shimizu N, Fujioka H. Chem. Commun. 2014; 50: 12530
    • 7d Arai T, Sugiyama N, Masu H, Kado S, Yabe S, Yamanaka M. Chem. Commun. 2014; 50: 8287
    • 7e Wilking M, Daniliuc CG, Hennecke U. Synlett 2014; 25: 1701
    • 7f Nakatsuji H, Sawamura Y, Sakakura A, Ishihara K. Angew. Chem. Int. Ed. 2014; 53: 6974
    • 7g Murai K, Nakamura A, Matsushita T, Shimura M, Fujioka H. Chem. Eur. J. 2012; 18: 8448
    • 7h Wang Y.-M, Wu J, Hoong C, Rauniyar V, Toste FD. J. Am. Chem. Soc. 2012; 134: 12928
    • 7i Paull DH, Fang C, Donald JR, Pansick AD, Martin SF. J. Am. Chem. Soc. 2012; 134: 11128
    • 7j Dobish MC, Johnston JN. J. Am. Chem. Soc. 2012; 134: 6068
    • 7k Denmark SE, Burk MT. Org. Lett. 2012; 14: 256
    • 7l Müller CH, Rösner C, Hennecke U. Chem. Asian J. 2014; 9: 2162
    • 7m Wilking M, Daniliuc CG, Hennecke U. Chem. Eur. J. 2016; 22: 18601
    • 7n Aursnes M, Tungen JE, Hansen TV. J. Org. Chem. 2016; 81: 8287

      Selected recent endeavors on the development of asymmetric N-type halocyclization:
    • 8a Huang H, Pan H, Cai Y, Liu M, Tian H, Shi Y. Org. Biomol. Chem. 2015; 13: 3566
    • 8b Huang D, Liu X, Li L, Cai Y, Liu W, Shi Y. J. Am. Chem. Soc. 2013; 135: 8101
    • 8c Lozano O, Blesslet G, del Campo TM, Thompson AL, Giuffredi GT, Bettati M, Walker M, Borman R, Gouverneur V. Angew. Chem. Int. Ed. 2011; 50: 8105
    • 8d Huang D, Wang H, Xue F, Guan H, Li L, Peng X, Shi Y. Org. Lett. 2011; 13: 6350

      Selected recent endeavors on the development of asymmetric haloaminocyclization:
    • 9a Cai Y, Zhou P, Liu X, Zhao J, Lin L, Feng X. Chem. Eur. J. 2015; 21: 6386
    • 9b Xie W, Jiang G, Liu H, Hu J, Pan X, Zhang H, Wan X, Lai Y, Ma D. Angew. Chem. Int. Ed. 2013; 52: 12924
    • 9c Tripathi CB, Murkherjee S. Org. Lett. 2014; 16: 3368

      Other selected examples:
    • 10a Chen Z.-M, Zhang Q.-W, Chen Z.-H, Li H, Tu Y.-Q, Zhang F.-M, Tian J.-M. J. Am. Chem. Soc. 2011; 133: 8818
    • 10b Li H, Zhang F.-M, Tu Y.-Q, Zhang Q.-W, Chen Z.-M, Chen Z.-H, Li J. Chem. Sci. 2011; 2: 1839
    • 10c Müller CH, Wilking M, Rühlmann A, Wibbeling B, Hennecke U. Synlett 2011; 2043
    • 10d Nicolaou KC, Simmons NL, Ying Y, Heretsch PM, Chen JS. J. Am. Chem. Soc. 2011; 133: 8134
    • 10e Kawato Y, Ono H, Kubota A, Nagao Y, Morita N, Egami H, Hamashima Y. Chem. Eur. J. 2016; 22: 2127
    • 11a Jiang X, Liu S, Yang S, Jing MX. L, Yu P, Wang Y, Yeung Y.-Y. Org. Lett. 2018; 20: 3259
    • 11b Li D, He H, Huang X, Yu P, Jiang X. SynOpen 2018; 2: 292

      Selected examples of α,β-unsaturated electrophiles:
    • 12a Wu Y, Hu L, Li Z, Deng L. Nature 2015; 523: 445
    • 12b Hu B, Bezpalko MW, Fei C, Dickie DA, Foxman BM, Deng L. J. Am. Chem. Soc. 2018; 140: 13913
    • 12c Hu B, Deng L. Angew. Chem. Int. Ed. 2018; 57: 2233
  • 13 The details are presented in the Supporting Information. CCDC 1911858 contains supplementary crystallographic data for compound 4b. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
  • 14 General Procedure for Bromolactonization. To a PhMe/CHCl3 (4 mL/1 ml) solution of α,β-unsaturated ketone (0.1 mmol, 1.0 equiv) and catalyst (7.1 mg, 0.15 mmol, 0.15 equiv) at 15°C, in dark under nitrogen was added halogen source (0.13 mmol, 1.3 equiv). The resulting mixture was stirred at 15°C and monitored by TLC. The reaction was quenched with saturated Na2SO3 (1 mL) at 15oC and then was warm to room temperature. The solution was diluted with water (3 mL) and extrated with EtOAc, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography (hexane/EtOAc=3:1) to yield the corresponding lactone. Supporting Information provides full details and graphical guide.