A Straightforward and Practical Approach to Chiral Inducer: (2R,3R)-1,4-Dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol
Jin-Sheng Xie A , Xiao-Yun Hu A C , Zi-Xing Shan B C and Zhong-Qiang Zhou A
+ Author Affiliations
- Author Affiliations
A College of Chemistry and Materials, South-Central University for Nationalities, Wuhan, China.
B College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, China.
C Corresponding authors. Email: xyhu@mail.scuec.edu.cn, zxshan@whu.edu.cn
Australian Journal of Chemistry 68(6) 995-998 https://doi.org/10.1071/CH14505
Submitted: 14 August 2014 Accepted: 8 October 2014 Published: 22 December 2014
Abstract
A straightforward and practical access to chiral inducer (2R,3R)-1,4- dimethoxyl-1,1,4,4-tetraphenyl-2,3-diol has been developed. It is based on highly regioselective 2,3-cyclosulfitation of (2R,3R)-1,1,4,4-tetraphenyl-butanetetraol, in which selective protection of the secondary hydroxyls and chlorination of the tertiary hydroxyls of (2R,3R)-1,1,4,4-tetraphenyl-butanetetraol are accomplished via one step. In the preparation, methanol was used as a methylating reagent and common alkali liquor was used for cleavage of the protection group. It may be one of the most straightforward and practical syntheses of the title compound.
References
[1] C. A. Berg, N. C. Eichenauer, J. Pietruszka, Pure Appl. Chem. 2012, 84, 2339.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhsFantLs%3D&md5=61a6350b573c7d381ea3a34e9d07cb18CAS |
[2] J. E. A. Luithle, J. Pietruszka, J. Org. Chem. 1999, 64, 8287.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXmsVensrg%3D&md5=0358ed95666d08acd5014fe15692dd48CAS |
[3] E. Fernández, W. Frey, J. Pietruszka, Synlett 2010, 1386.
| Crossref | GoogleScholarGoogle Scholar |
[4] J. Pietruszka, N. Schöne, Angew. Chem., Int. Ed. 2003, 42, 5638.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXpsl2ktL0%3D&md5=da66e634fc2147c352cb3f4cbd9a6fb6CAS |
[5] V. Cmrecki, N. C. Eichenauer, W. Frey, J. Pietruszka, Tetrahedron 2010, 66, 6550.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXptlaqt70%3D&md5=f9e052e6cc20c99be10f9bff7e521c95CAS |
[6] R. Vahabi, W. Frey, J. Pietruszka, J. Org. Chem. 2013, 78, 11549.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhs1CktrbK&md5=7c0690082710551390d6469d31e850a9CAS | 24195579PubMed |
[7] E. Fernández, J. Pietruszka, W. Frey, J. Org. Chem. 2010, 75, 5580.
| Crossref | GoogleScholarGoogle Scholar | 20672807PubMed |
[8] D. Böse, P. Niesobski, M. Lübcke, J. Pietruszka, J. Org. Chem. 2014, 79, 4699.
| Crossref | GoogleScholarGoogle Scholar | 24745807PubMed |
[9] J. Pietruszka, A. Rieche, Adv. Synth. Catal. 2008, 350, 1407.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXnvFWmtLg%3D&md5=fc20711110c623db9003238f37e85fe0CAS |
[10] D. Böse, E. Fernández, J. Pietruszka, J. Org. Chem. 2011, 76, 3463.
| Crossref | GoogleScholarGoogle Scholar | 21434691PubMed |
[11] N. Ty, R. Pontikis, G. Chabot, E. Devillers, L. Quentin, S. Bourg, J. C. Florent, Bioorg. Med. Chem. 2013, 21, 1357.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhs1ensbc%3D&md5=17639e6cbf325dca41b0b6654cfac0fdCAS | 23369686PubMed |
[12] S. Bartlett, D. Böse, D. Ghori, B. Mechsner, J. Pietruszka, Synthesis 2013, 45, 1106.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXps1Oqu7Y%3D&md5=e012099807935e12cadb9776c904476eCAS |
[13] K. Nakayama, J. D. Rainier, Tetrahedron 1990, 46, 4165.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXlvFWh&md5=7f0c890de14ff1e9ba2e9e5686fadbb5CAS |
[14] S. Srimurugan, P. Suresh, B. Viswanathan, T. K. Varadarajan, Synth. Commun. 2007, 37, 2483.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXovFSru7g%3D&md5=420b5fc29262e66f1e2812ec3d9a7514CAS |
[15] M. Bischop, V. Cmrecki, V. Ophoven, J. Pietruszka, Synthesis 2008, 2488.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXpvVOltLs%3D&md5=7ae0b7e463ce5b719969ff95705e1b57CAS |
[16] X. Y. Hu, Z. X. Shan, S. J. Song, Tetrahedron: Asymmetry 2014, 25, 503.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXksFyrsbk%3D&md5=742170a7495a33a870a0fc1b6921e356CAS |
[17] X. Y. Hu, Z. X. Shan, V. A. Soloshonok, Cryst. Growth Des. 2012, 12, 33.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsVCrsLrE&md5=bf9c4af55392cebf7278bb5efe1ea279CAS |
[18] Z. X. Shan, X. Y. Hu, Y. Zhou, X. T. Peng, Z. Li, Helv. Chim. Acta 2010, 93, 497.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXjtlamsbY%3D&md5=f8ba1547c4355d8937cf68e0bd14dde3CAS |
[19] X. Y. Hu, Z. X. Shan, X. T. Peng, Z. Li, Tetrahedron: Asymmetry 2009, 20, 2474.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsFaku73P&md5=132eb6dcd9d5489c7cc61b37d4f4b061CAS |
[20] Z. X. Shan, X. Y. Hu, Y. Zhou, X. T. Peng, J. Yi, Tetrahedron: Asymmetry 2009, 20, 1445.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXosVGjtbo%3D&md5=e4f1d2ba9bfdfcc6bc5e23dcf57270bbCAS |
[21] X. Y. Hu, Z. X. Shan, Q. Chang, Lett. Org. Chem. 2012, 9, 493.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhsVegu7zM&md5=30992b08670caedc993ef178923d4b2aCAS |
[22] D. Seebach, A. K. Beck, A. Heckel, Angew. Chem., Int. Ed. 2001, 40, 92.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXltlKguw%3D%3D&md5=6b860a16e1e7e56bdc99088c6eee8b64CAS |
[23] D. Seebach, A. Pichota, A. K. Beck, A. B. Pinkerton, T. Litz, J. Karjalainen, V. Gramlich, Org. Lett. 1999, 1, 55.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXjt1aqtbk%3D&md5=2c15f3be04a6689d64bca3ee14a324e4CAS |
[24] D. Seebach, M. Hayakawa, J. Sakaki, W. B. Schweizer, Tetrahedron 1993, 49, 1711.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXisFGjsLc%3D&md5=26c5b7162ce311cbfe5c653fc275ff7eCAS |
