Synthesis of Chiral 1,2-Dihydronaphtho[2,1-b]furans by Organocatalytic Domino Reactions Catalyzed with Multiple Catalysis
Jin-Yun Pan A , Xin-Sheng Li A , Dong-Cheng Xu A and Jian-Wu Xie A B
+ Author Affiliations
- Author Affiliations
A Department of Chemistry and Life Science, Zhejiang Normal University, 321004 Jinhua, China.
B Corresponding author. Email: xiejw@zjnu.cn
Australian Journal of Chemistry 66(11) 1415-1421 https://doi.org/10.1071/CH13317
Submitted: 23 June 2013 Accepted: 26 July 2013 Published: 28 August 2013
Abstract
A chiral multiple catalysis with two chiral units has been proved effective in the domino Friedel–Crafts alkylation of β-naphthols with α-bromonitroalkenes. This novel and efficient domino reaction affords chiral 1,2-dihydronaphtho[2,1-b]furans in good to high yields and enantioselectivities (up to 93 % yield, 91 % enantiomeric excess).
References
[1] B. H. Lipshutz, Chem. Rev. 1986, 86, 795.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28XlsFartrw%3D&md5=972805e18621c4d7dabe339e69c10f0eCAS |
[2] R. Benassi, in Comprehensive Heterocyclic Chemistry II (Eds A. R. Katritzky, C. W. Rees, E. F. V. Scriven) 1996, Vol. 2, pp. 259–295 (Pergamon Press: Oxford).
[3] B. A. Keay, P. W. Dibble, in Comprehensive Heterocyclic Chemistry II (Eds A. R. Katritzky, C. W. Rees, E. F. V. Scriven) 1996, Vol. 4, pp. 395–436 (Pergamon Press: Oxford).
[4] G. A. Kraus, N. Zhang, J. G. Verkade, M. Nagarajan, P. B. Kisanga, Org. Lett. 2000, 2, 2409.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXksleisr8%3D&md5=664641a7e745c18d567a4f4536dfb89cCAS | 10956508PubMed |
[5] (a) H. Hagiwara, K. Sato, T. Suzuki, M. Ando, Heterocycles 1999, 51, 497.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXhslygur0%3D&md5=588465ce6d82f727f0760e5d56cb2eacCAS |
(b) H. Hagiwara, K. Sato, D. Nishino, T. Hoshi, T. Suzuki, M. J. Ando, J. Chem. Soc., Perkin Trans. 1 2001, 1, 2946.
| Crossref | GoogleScholarGoogle Scholar |
[6] (a) J. J. Chambers, D. M. Kurrasch-Orbaugh, M. A. Parker, D. E. Nichols, J. Med. Chem. 2001, 44, 1003.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXmtF2jsw%3D%3D&md5=650660b9cfe51948cc4972a558754965CAS | 11300881PubMed |
(b) L. Rene, J.-P. Buisson, R. Royer, D. Averbeck, Eur. J. Med. Chem. 1977, 12, 31.
(c) C. Bilger, P. Demerseman, J. P. Buisson, R. Royer, P. Gayral, J. Fourniat, Eur. J. Med. Chem. 1987, 22, 213.
| Crossref | GoogleScholarGoogle Scholar |
[7] G. A. Kraus, N. Zhang, J. G. Verkade, M. Nagarajan, P. B. Kisanga, Org. Lett. 2000, 2, 2409.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXksleisr8%3D&md5=664641a7e745c18d567a4f4536dfb89cCAS | 10956508PubMed |
[8] (a) K. C. Nicolaou, S. A. Snyder, A. Bigot, J. A. Pfefferkora, Angew. Chem. Int. Ed. 2000, 39, 1093.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXisVCqtrc%3D&md5=e2541f577aeba850d77172f736cce65fCAS |
(b) J. Habermann, S. V. Ley, R. Smits, J. Chem. Soc., Perkin Trans. 1 1999, 1, 2421.
| Crossref | GoogleScholarGoogle Scholar |
(c) H. M. Meshram, K. C. Sekhar, Y. S. S. Ganesh, J. S. Yadav, Synlett 2000, 1273.
(d) Z. Chen, X. Wang, W. Lu, J. Yu, Synlett 1991, 121.
| Crossref | GoogleScholarGoogle Scholar |
[9] (a) K. K. Park, H. Seo, J.-G. Kim, I.-H. Suh, Tetrahedron Lett. 2000, 41, 1393.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXhslSnu7k%3D&md5=08f36ebef48bb08034331a4eb9150892CAS |
(b) K. K. Park, I. K. Han, J. W. Park, J. Org. Chem. 2001, 66, 6800.
| Crossref | GoogleScholarGoogle Scholar |
(c) A. R. Katritzky, Y. Ji, Y. Fang, I. Prakash, J. Org. Chem. 2001, 66, 5613.
| Crossref | GoogleScholarGoogle Scholar |
(d) X. Xie, B. Chen, J. Lu, J. Han, X. She, X. Pan, Tetrahedron Lett. 2004, 45, 6235.
| Crossref | GoogleScholarGoogle Scholar |
(e) M. del Carmen Cruz, J. Tamariz, Tetrahedron Lett. 2004, 45, 2377.
| Crossref | GoogleScholarGoogle Scholar |
[10] (a) H. Hagiwara, K. Sato, T. Suzuki, M. Ando, Heterocycles 1999, 51, 497.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXhslygur0%3D&md5=588465ce6d82f727f0760e5d56cb2eacCAS |
(b) H. Hagiwara, K. Sato, D. Nishino, T. Hoshi, T. Suzuki, M. Ando, J. Chem. Soc., Perkin Trans. 1 2001, 1, 2946.
| Crossref | GoogleScholarGoogle Scholar |
[11] (a) I. Yavari, M. Anary-Abbasinejad, A. Alizadeh, Tetrahedron Lett. 2002, 43, 4503.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xktlygu7s%3D&md5=7249dbef8fb866e697cb34d9e36abf6bCAS |
(b) M. Jørgensen, F. C. Krebs, K. J. Bechgaard, J. Org. Chem. 2000, 65, 8783.
| Crossref | GoogleScholarGoogle Scholar |
(c) A. R. Katritzky, L. Serdyuk, L. Xie, J. Chem. Soc., Perkin Trans. 1 1998, 1, 1059.
| Crossref | GoogleScholarGoogle Scholar |
(d) J. N. Chatterjea, V. N. Mehrotra, S. K. Roy, Chem. Ber. 1963, 96, 1167.
| Crossref | GoogleScholarGoogle Scholar |
(e) V. K. Mahesh, R. Sharma, M. Maheshwari, Indian J. Chem. 1979, 17, 528.
[12] C. Jarava-Barrera, F. Esteban, C. Navarro-Ranninger, A. Parra, J. Alemán, Chem. Commun. 2013, 49, 2001.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXitlCitL4%3D&md5=f8f0ddd33df13cc94217d90e94c4c20dCAS |
[13] (a) M. Abdul-Aziz, J. V. Auping, M. A. Meador, J. Org. Chem. 1995, 60, 1303.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXjvFOrsLw%3D&md5=001d7f42d78c5910ba1b01d19bd83e16CAS |
(b) K. K. Park, H. Lim, S.-H. Kim, D. H. Bae, J. Chem. Soc., Perkin Trans. 1 2002, 1, 310.
| Crossref | GoogleScholarGoogle Scholar |
(c) K. K. Park, H. Lim, Heterocycles 2002, 57, 657.
| Crossref | GoogleScholarGoogle Scholar |
(d) K. K. Park, S.-H. Kim, J. W. Park, J. Photochem. Photobiol. Chem. 2004, 163, 241.
| Crossref | GoogleScholarGoogle Scholar |
(e) P. K. Frederiksen, M. Jørgensen, P. R. Ogilby, J. Am. Chem. Soc. 2001, 123, 1215.
| Crossref | GoogleScholarGoogle Scholar |
(f) T. D. Poulsen, P. K. Frederiksen, M. Jørgensen, K. V. Mikkelsen, P. R. Ogilby, J. Phys. Chem. A 2001, 105, 11488.
| Crossref | GoogleScholarGoogle Scholar |
[14] L.-P. Fan, X.-S. Li, D.-C. Xu, M.-M. Ge, W.-D. Zhu, J.-W. Xie, J. Org. Chem. 2010, 75, 8716.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhsVGksbfL&md5=e486b481b0d1ea2dee329f259c21da6aCAS | 21090776PubMed |
[15] (a) S. H. McCooey, S. J. Connon, Angew. Chem. Int. Ed. 2005, 117, 6525.
| Crossref | GoogleScholarGoogle Scholar |
(b) B. Vakulya, S. Varga, A. Csampai, T. Soos, Org. Lett. 2005, 7, 1967.
| Crossref | GoogleScholarGoogle Scholar |
[16] (a) T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXns1Wmtbg%3D&md5=72621736314d92e91eb6638494a46247CAS | 14558791PubMed |
(b) T. Okino, Y. Hoashi, T. Furukawa, X. Xu, Y. Takemoto, J. Am. Chem. Soc. 2005, 127, 119.
| Crossref | GoogleScholarGoogle Scholar |
[17] C.-L. Cao, M.-C. Ye, X.-L. Sun, Y. Tang, Org. Lett. 2006, 8, 2901.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XlvFentb8%3D&md5=7ffe481be27e85ed50c452c009dc55b4CAS | 16805512PubMed |
[18] S. Piovesana, D. M. Scarpino Schietroma, M. Bella, Angew. Chem. Int. Ed. 2011, 50, 6216.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXmsValsb4%3D&md5=606b917e764826188894401cb1c94b72CAS |
[19] W. L. F. Armarego, D. D. Perrin, Purification of Laboratory Chemicals 1997, 4th edn (Butterworth Heinemann: Oxford).
