Lewis Acid Catalyzed [3+2] Coupling of Quinone Monoacetals or Quinone Imine Ketals with Vinylcarbamates

Li-Hua Liao; Min-Min Zhang; Yi-Jun Liao; Wei-Cheng Yuan; Xiao-Mei Zhang

doi:10.1055/s-0034-1380723

Synlett, Table of Contents

Synlett 2015; 26(12): 1720-1724
DOI: 10.1055/s-0034-1380723

letter

Lewis Acid Catalyzed [3+2] Coupling of Quinone Monoacetals or Quinone Imine Ketals with Vinylcarbamates

Li-Hua Liao

^aKey Laboratory for Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China Email: xmzhang@cioc.ac.cn

^bUniversity of Chinese Academy of Sciences, Beijing, 100049, P. R. of China

,

Min-Min Zhang

^aKey Laboratory for Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China Email: xmzhang@cioc.ac.cn

^bUniversity of Chinese Academy of Sciences, Beijing, 100049, P. R. of China

,

Yi-Jun Liao

^aKey Laboratory for Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China Email: xmzhang@cioc.ac.cn

^bUniversity of Chinese Academy of Sciences, Beijing, 100049, P. R. of China

,

Wei-Cheng Yuan

^aKey Laboratory for Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China Email: xmzhang@cioc.ac.cn

,

Xiao-Mei Zhang*

^aKey Laboratory for Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China Email: xmzhang@cioc.ac.cn

› Author Affiliations

Abstract

All articles of this category

Abstract

A mild and concise [3+2] coupling of quinone monoacetals or quinone imine ketals with vinylcarbamates promoted by Lewis acid was realized. Various 2-carbamate-2,3-dihydrobenzofurans and 2-carbamate-indolines have been prepared in moderate to good yields.

Key words

[3+2] coupling - Lewis acid - synthesis - 2-carbamate-2,3-dihydrobenzofurans - 2-carbamate-indolines

Full Text

References

References and Notes

For reviews, see:

1a Ward RS. Chem. Soc. Rev. 1982; 11: 75
1b Proksch P, Rodriquez E. Phytochemistry 1983; 22: 2335

For some recent examples, see:

2a Pettersson M, Johnson DS, Subramanyam C, Bales KR, Ende CW. A, Fish BA, Green ME, Kauffman GW, Lira R, Mullins PB, Navaratnam T, Sakya SM, Stiff CM, Tran TP, Vetelino BC, Xie LF, Zhang LM, Pustilnik LR, Wood KM, O’Donnell CJ. Bioorg. Med. Chem. Lett. 2012; 22: 2906
2b Mayaka RK, Langat MK, Omolo JO, Cheplogoi PK. Planta Med. 2012; 78: 383
2c Shen F, Hu AX, Luo XF, Ye J, Ou XM. Chin. J. Org. Chem. 2012; 32: 388
2d Vijayakurup V, Carmela S, Carmelo D, Corrado T, Srinivas P, Gopala S. Life Sci. 2012; 91: 1336
2e Chen W, Yang XD, Li Y, Yang LJ, Wang XQ, Zhang GL, Zhang HB. Org. Biomol. Chem. 2011; 9: 4250
2f Jiao WH, Gao H, Zhao F, He F, Zhou GX, Yao XS. Chemistry & Biodiversity 2011; 8: 1163
2g Yang F, Zhang HJ, Zhang YY, Chen WS, Yuan HL, Lin HW. Chem. Pharm. Bull. 2010; 58: 402
2h Bose JS, Gangan V, Prakash R, Jain SK, Manna SK. J. Med. Chem. 2009; 52: 3184
2i Frampton JE. Drugs 2009; 69: 2463
2j Ha DT, Tran MN, Lee I, Lee YM, Kim JS, Jung H, Lee S, Na M, Bae K. J. Nat. Prod. 2009; 72: 1465
2k Gupta D, Bleakley B, Gupta RK. J. Ethnopharmacol. 2008; 115: 361
2l Saito M, Ueo M, Kametaka S, Saigo O, Uchida S, Hosaka H, Sakamoto K, Nakahara T, Mori A, Ishii K. Biol. Pharm. Bull. 2008; 31: 1959
2m Pongcharoen W, Rukachaisirikul V, Phongpaichit S, Sakayaroj J. Chem. Pharm. Bull. 2007; 55: 1404
2n Yang XW, Zhao PJ, Ma YL, Xiao HT, Zuo YQ, He HP, Li L, Hao XJ. J. Nat. Prod. 2007; 70: 521
2o Jang JH, Kanoh K, Adachi K, Shizuri Y. J. Antibiot. 2006; 59: 428
2p Wakana D, Hosoe T, Itabashi T, Okada K, Takaki GM. D, Yaguchi T, Fukushima K, Kawai K. J. Nat. Med. 2006; 60: 279
2q Shi GQ, Dropinski JF, Zhang Y, Santini C, Sahoo SP, Berger JP, MacNaul KL, Zhou GC, Agrawal A, Alvaro R, Cai TQ, Hernandez M, Wright SD, Moller DE, Heck JV, Meinke PT. J. Med. Chem. 2005; 48: 5589
2r Pang JY, Xu ZL. Chin. J. Org. Chem. 2005; 25: 25
2s Van Miert S, Van Dyck S, Schmidt TJ, Brun R, Vlietinck A, Lemiere G, Pieters L. Bioorg. Med. Chem. 2005; 13: 661
2t Tanaka H, Hirata M, Etoh H, Sako M, Sato M, Murata J, Murata H, Darnaedi D, Fukai T. Chemistry & Biodiversity 2004; 1: 1101
2u Li RW, Leach DN, Myers SP, Lin GL. D, Leach GJ, Waterman PG. Planta Med. 2004; 70: 421
2v Pauwels PJ, Rauly I, Wurch T. J. Pharmacol. Exp. Ther. 2003; 305: 1015
2w Inagaki M, Jyoyama H, Ono T, Yamada K, Kobayashi M, Baba T, Touchi A, Iwatani K, Ohkawa T, Matsumoto S, Tsuri T. Bioorg. Med. Chem. 2003; 11: 2415
2x Chen CH, Shaw CY, Chen CC, Tsai YC. J. Nat. Prod. 2002; 65: 740
2y Saeki M, Sakai M, Saito R, Kubota H, Ariumi H, Takano Y, Yamatodani A, Kamiya H. Jpn. J. Pharmacol. 2001; 86: 359
2z Cho JY, Baik KU, Yoo ES, Yoshikawa K, Park MH. J. Nat. Prod. 2000; 63: 1205

For reviews, see:

3a Sheppard TD. J. Chem. Res. 2011; 377
3b Pu WC, Wang F, Wang C. Chin. J. Org. Chem. 2011; 31: 155
3c Bertolini F, Pineschi M. Org. Prep. Proced. Int. 2009; 41: 385

For some recent examples, see:

4a Cong H, Fu GC. J. Am. Chem. Soc. 2014; 136: 3788
4b Blum TR, Zhu Y, Nordeen SA, Yoon TP. Angew. Chem. Int. Ed. 2014; 53: 11056
4c Belmessieri D, de la Houpliere A, Calder ED. D, Taylor JE, Smith AD. Chem. Eur. J. 2014; 20: 9762
4d Ueda M, Ito Y, Ichii Y, Kakiuchi M, Shono H, Miyata O. Chem. Eur. J. 2014; 20: 6763
4e Wu B, Chen MW, Ye ZS, Yu CB, Zhou YG. Adv. Synth. Catal. 2014; 356: 383
4f Shaikh AK, Varvounis G. Org. Lett. 2014; 16: 1478
4g Fujita T, Sanada S, Chiba Y, Sugiyama K, Ichikawa J. Org. Lett. 2014; 16: 1398
4h Jiang SS, Hu B, Yu XX, Deng WP. Chin. J. Chem. 2014; 32: 694
4i Hata K, He ZH, Daniliuc CG, Itami K, Studer A. Chem. Commun. 2014; 50: 463
4j Luo LG, Liu CZ, Hou ZQ, Wang YY, Dai LY. RSC Adv. 2014; 4: 29527
4k Ito M, Namie R, Krishnamurthi J, Miyamae H, Takeda K, Nambu H, Hashimoto S. Synlett 2014; 25: 288
4l Ortega N, Urban S, Beiring B, Glorius F. Angew. Chem. Int. Ed. 2012; 51: 1710
4m Tsui GC, Tsoung J, Dougan P, Lautens M. Org. Lett. 2012; 14: 5542
4n Zhao GQ, Wang BJ, Yang WJ, Ren HJ. Eur. J. Org. Chem. 2012; 6236
4o Ortega N, Beiring B, Urban S, Glorius F. Tetrahedron 2012; 68: 5185
4p Wang DH, Yu JQ. J. Am. Chem. Soc. 2011; 133: 5767
4q Belmessieri D, Morrill LC, Simal C, Slawin AM. Z, Smith AD. J. Am. Chem. Soc. 2011; 133: 2714
4r Senboku H, Michinishi J, Hara S. Synlett 2011; 1567
4s Samant BS, Bhagwat SS. Chin. J. Catal. 2011; 32: 231
4t Gharpure SJ, Prasath V. J. Chem. Sci. 2011; 123: 943
4u Baragona F, Lomberget T, Duchamp C, Henriques N, Lo Piccolo E, Diana P, Montalbano A, Barret R. Tetrahedron 2011; 67: 8731
4v Uyanik M, Okamoto H, Yasui T, Ishihara K. Science 2010; 328: 1376
4w Xie PZ, Huang Y, Chen RY. Org. Lett. 2010; 12: 3768

For coupling of quinone derivatives with alkene nucleophiles, see:

5a Hu Y, Kamitanaka T, Mishima Y, Dohi T, Kita Y. J. Org. Chem. 2013; 78: 5530
5b Dohi T, Hu YJ, Kamitanaka T, Washimi N, Kita Y. Org. Lett. 2011; 13: 4814
5c Dohi T, Hu YJ, Kamitanaka T, Kita Y. Tetrahedron 2012; 68: 8424
5d Lomberget T, Baragona F, Fenet B, Barret R. Org. Lett. 2006; 8: 3919
5e Zhou G, Corey EJ. J. Am. Chem. Soc. 2005; 127: 11958
5f Nair V, Rajesh C, Dhanya R, Rath NP. Org. Lett. 2002; 4: 953
5g Apers S, Paper D, Bürgermeister J, Baronikova S, Van Dyck S, Lemiere G, Vlietinck A, Pieters L. J. Nat. Prod. 2002; 65: 718
5h Ohara H, Kiyokane H, Itoh T. Tetrahedron Lett. 2002; 43: 3041
5i Itoh T, Kawai K, Hayase S, Ohara H. Tetrahedron Lett. 2003; 44: 4081
5j Benbow JW, Katoch-Rouse R. J. Org. Chem. 2001; 66: 4965
5k Engler TA, Letavic MA, Iyengar R, LaTessa KO, Reddy JP. J. Org. Chem. 1999; 64: 2391
5l Bolzacchini E, Brunow G, Meinardi S, Orlandi M, Rindone B, Rummakko P, Setala H. Tetrahedron Lett. 1998; 39: 3291
5m Engler TA, Chai W, LaTessa KO. J. Org. Chem. 1996; 61: 9297
5n Engler TA, Gfesser GA, Draney BW. J. Org. Chem. 1995; 60: 3700
5o Lemière G, Gao M, De Groot A, Dommisse R, Lepoivre J, Pieters L, Buss V. J. Chem. Soc., Perkin Trans. 1 1995; 1775
5p Kerns ML, Conroy SM, Swenton JS. Tetrahedron Lett. 1994; 35: 7529
5q Wang SP, Gates BD, Swenton JS. J. Org. Chem. 1991; 56: 1979
5r Engler TA, Combrink KD, Ray JE. J. Am. Chem. Soc. 1988; 110: 7931

For reviews, see:

6a Magdziak D, Meek SJ, Pettus TR. R. Chem. Rev. 2004; 104: 1383
6b Liao CC, Peddinti RK. Acc. Chem. Res. 2002; 35: 856

For some recent examples, see:

6c Nishiyama Y, Han-Ya Y, Yokoshima S, Fukuyama T. J. Am. Chem. Soc. 2014; 136: 6598
6d Zhang YC, Zhao JJ, Jiang F, Sun SB, Shi F. Angew. Chem. Int. Ed. 2014; 53: 13912
6e Zhang YC, Jiang F, Wang SL, Shi F, Tu SJ. J. Org. Chem. 2014; 79: 6143
6f Yin ZW, Zhang JZ, Wu J, Green R, Li SH, Zheng SP. Org. Biomol. Chem. 2014; 12: 2854
6g Liao LH, Shu C, Zhang MM, Liao YJ, Hu XY, Zhang YH, Wu ZJ, Yuan WC, Zhang XM. Angew. Chem. Int. Ed. 2014; 53: 10471
6h Shu C, Liao LH, Liao YJ, Hu XY, Zhang YH, Yuan WC, Zhang XM. Eur. J. Org. Chem. 2014; 4467
6i Zhang YH, Hu XY, Li SS, Liao YJ, Yuan WC, Zhang XM. Tetrahedron 2014; 70: 2020
6j Hashimoto T, Nakatsu H, Takiguchi Y, Maruoka K. J. Am. Chem. Soc. 2013; 135: 16010
6k Ito M, Kubo H, Itani I, Morimoto K, Dohi T, Kita Y. J. Am. Chem. Soc. 2013; 135: 14078
6l Zhang JZ, Yin ZW, Leonard P, Wu J, Sioson K, Liu C, Lapo R, Zheng SP. Angew. Chem. Int. Ed. 2013; 52: 1753
6m Albrecht Ł, Gómez CV, Jacobsen CB, Jørgensen KA. Org. Lett. 2013; 15: 3010
6n Han ZY, Chen DF, Wang YY, Guo R, Wang PS, Wang C, Gong LZ. J. Am. Chem. Soc. 2012; 134: 6532
6o He ZL, Liu TL, Tao HY, Wang CJ. Org. Lett. 2012; 14: 6230
6p Wang J, Wang S, Wang G, Zhang J, Yu XQ. Chem. Commun. 2012; 48: 11769
6q Siau WY, Li WJ, Xue F, Ren Q, Wu MH, Sun SF, Guo HB, Jiang XF, Wang J. Chem. Eur. J. 2012; 18: 9491
6r Yu JS, Zhou F, Liu YL. Zhou J. Beilstein J. Org. Chem. 2012; 8: 1360
6s Liu YJ, Liu JX, Wang M, Liu J, Liu Q. Adv. Synth. Catal. 2012; 354: 2678
6t Dohi T, Washimi N, Kamitanaka T, Fukushima K, Kita Y. Angew. Chem. Int. Ed. 2011; 50: 6142
6u Fujiwara Y, Domingo V, Seiple IB, Gianatassio R, Bel MD, Baran PS. J. Am. Chem. Soc. 2011; 133: 3292
6v Chuang KV, Navarro R, Reisman SE. Chem. Sci. 2011; 2: 1086
6w Tian W, Chennamaneni LR, Suzuki T, Chen DY.-K. Eur. J. Org. Chem. 2011; 1027
6x Jensen KL, Franke PT, Nielsen LT. K, Daasbjerg K, Jørgensen KA. Angew. Chem. Int. Ed. 2010; 49: 129
6y Wang C, Chen XH, Zhou SM, Gong LZ. Chem. Commun. 2010; 46: 1275

For some recent examples of on formal [3+2] cycloadditions or [3+2] annulations, see:

7a Shi F, Zhang HH, Sun XX, Liang J, Fan T, Tu SJ. Chem. Eur. J. 2015; 21: 3465
7b Ball-Jones NR, Badillo JJ, Tran NT, Franz AK. Angew. Chem. Int. Ed. 2014; 53: 9462
7c Xuan J, Xia XD, Zeng TT, Feng ZJ, Chen JR, Lu LQ, Xiao WJ. Angew. Chem. Int. Ed. 2014; 53: 5653
7d Tan W, Li X, GongY X, Ge MD, Shi F. Chem. Commun. 2014; 50: 15901
7e Zhu FL, Wang YH, Zhang DY, Xu J, Hu XP. Angew. Chem. Int. Ed. 2014; 53: 10223

8 General Experimental Procedure for the [3+2] Coupling of Quinone Monoacetals or Quinone Imine Ketals 1 with Vinylcarbamates 2 Quinone monoacetal or quinone imine ketal 1 (0.30 mmol) and vinylcarbamate 2 (0.20 mmol) were added to a flame-dried vial equipped with a magnetic stirring bar. Then MeCN (2 mL) was added to dissolve the mixture. Afterwards Cu(OTf)₂ (10.8 mg, 0.02 mmol) was introduced in the solution. The reaction mixture was stirred at 25 °C for 12 h. Then the solvent was evaporated, and the residue was subjected to chromatography (silica gel; hexane–EtOAc, 20:1 to 10:1) to afford the desired product 3.
9 Benzyl (5-Methoxy-2,3-dihydrobenzofuran-2-yl)carbamate (3a) Yield 84%, 0.050 g; white solid. ¹H NMR (300 MHz, CDCl₃): δ = 7.26–7.35 (m, 5 H), 6.65–6.74 (m, 3 H), 6.26 (br s, 1 H), 5.75 (d, J = 8.8 Hz, 1 H), 5.08–5.18 (m, 2 H), 3.74 (s, 3 H), 3.49 (dd, J ₁ = 8.3 Hz, J ₂ = 16.4 Hz, 1 H), 2.89 (dd, J ₁ = 16.5 Hz, J ₂ = 4.5 Hz, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 155.3, 154.3, 151.8, 135.8, 128.5, 128.3, 128.2, 125.2, 113.3, 110.9, 109.8, 85.3, 67.2, 55.9, 36.1. ESI-HRMS: m/z calcd for C₁₇H₁₇NO₄Na⁺ [M + Na]⁺: 322.1047; found: 322.1055.

Supplementary Material

Supporting Information