Oxidative Kinetic Resolution of cis-Fused Tricyclic 1-Tetralone Derivatives by Guanidine–Bisurea Bifunctional Organocatalyst
Received: 28 December 2016
Accepted after revision: 02 February 2017
24 February 2017 (online)
We present an enantioselective synthesis of cis-fused tricyclic 1-tetralones via oxidative kinetic resolution in the presence of cumene hydroperoxide (CHP) and guanidine–bisurea bifunctional organocatalyst. This reaction affords the corresponding α-hydroxylation products together with unreacted tetralones in good to high enantioselectivity, with s values as high as 42. The reaction was successfully applied for the synthesis of the core structure of a kainoid derivative, 4-(2-methoxyphenyl)-2-carboxy-3-pyrrolidineacetic acid (MFPA).
References and Notes
- 1 Neumeyer JL, Bidlack JM, Zong R, Bakthavachalam V, Gao P, Cohen DJ, Negus SS, Mello NK. J. Med. Chem. 2000; 43: 114-114
- 2 Wellington KD, Cambie RC, Rutledge PS, Bergquist PR. J. Nat. Prod. 2000; 63: 79-79
- 3 Singh AJ, Dattelbaum JD, Field JJ, Smart Z, Woolly EF, Barber JM, Heathcott R, Miller JH, Northcote PT. Org. Biomol. Chem. 2013; 11: 8041-8041
- 4 Yan YM, Ai J, Zhou LL, Chung AC, Li R, Nie J, Fang P, Wang XL, Luo J, Hu Q, Hou FF, Cheng YX. Org. Lett. 2013; 15: 5488-5488
- 5 Nicolaou KC, Gray D, Tae J. Angew. Chem. Int. Ed. 2001; 40: 3675-3675
- 6 Nicolaou KC, Gray D, Tae J. Angew. Chem. Int. Ed. 2001; 40: 3679-3679
- 7 Uenoyama Y, Tsukida M, Doi T, Ryu I, Studer A. Org. Lett. 2005; 7: 2985-2985
- 8 Sato T, Tamura K. Tetrahedron Lett. 1984; 25: 1821-1821
- 9 Duthaler RO, Ginsburg D. Helv. Chim. Acta 1986; 69: 1559-1559
- 10 Oh SH, Tamura K, Sato T. Tetrahedron 1992; 48: 9687-9687
- 11 Ramana MM. V, Potnis PV. Synthesis 1996; 1090-1090
- 12 Odagi M, Furukori K, Watanabe T, Nagasawa K. Chem. Eur. J. 2013; 19: 16740-16740
- 13 Odagi M, Furukori K, Yamamoto Y, Sato M, Iida K, Yamanaka M, Nagasawa K. J. Am. Chem. Soc. 2015; 137: 1909-1909
- 14 In the case of rac-4d, TS-4d-I is unfavorable compared to TS-4d-II (Scheme 5) due to steric repulsion between the cyclopentane moiety and methoxy group on the aromatic ring. On the other hand, TS-4d-II also exhibits steric repulsion between CHP and the carbon atom at C3 in rac-4d.
- 15 We have reported DFT calculation studies of the transition states of oxidative kinetic resolution.13 Based upon the calculations, we proposed transition state models of oxidation for rac-4i and rac-4j in Scheme 3 (TS-cis-I–IV and TS-trans-I–IV).
- 16a Hashimoto K, Horikawa M, Shirahama H. Tetrahedron Lett. 1990; 31: 7047-7047
- 16b Hashimoto K, Shirahama H. Tetrahedron Lett. 1991; 32: 2625-2625