Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2019; 51(04): 848-858
DOI: 10.1055/s-0037-1611277
DOI: 10.1055/s-0037-1611277
paper
Diastereoselective Synthesis of Cyclic sp3-Enriched cis-β-Alkoxysulfonyl Chlorides
This work was funded by Enamine Ltd.Further Information
Publication History
Received: 07 September 2018
Accepted after revision: 01 October 2018
Publication Date:
22 October 2018 (online)
Abstract
A three-step synthesis of β-alkoxy-substituted alicyclic sulfonyl chlorides from cyclic alkenes and alcohols is reported. The scope of the method was studied for a range of the substrates with various steric and electronic properties. The title compounds were obtained on a hundred-gram scale in up to 52% overall yield scale as single cis-diastereomers.
Key words
organosulfur compounds - alicyclic compounds - heteroaliphatic compounds - sulfonyl chlorides - building blocksSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611277.
- Supporting Information
-
References
- 1 Domagk G. Dtsch. Med. Wochenschr. 1935; 61: 250
- 2 According to ChEMBL database from march 2018; https://www.ebi.ac.uk/chembl.
- 3 Meng F, Chen N, Xu J. Sci. China Chem. 2012; 55: 2548
- 4 Shavnya A, Coffey SB, Hesp KD, Ross SC, Tsai AS. Org. Lett. 2016; 18: 5848
- 5 Shavnya A, Hesp KD, Tsai AS. Adv. Synth. Catal. 2018; 360: 1768
- 6 Tsai AS, Curto JM, Rocke BN, Dechert-Schmitt A.-MR, Ingle GK, Mascitti V. Org. Lett. 2016; 18: 508
- 7 Zhersh S, Buryanov V, Karpenko O, Grygorenko O, Tolmachev A. Synthesis 2011; 3669
- 8 Abdellaoui H, Chen X, Xu J. Synthesis 2017; 49: 2250
- 9 Bogolubsky AV, Moroz YS, Mykhailiuk PK, Pipko SE, Konovets AI, Sadkova IV, Tolmachev A. ACS Comb. Sci. 2014; 16: 192
- 10 Mykhalchuk VL, Yarmolchuk VS, Doroschuk RO, Tolmachev AA, Grygorenko OO. Eur. J. Org. Chem. 2018; 2870
- 11 Zhersh SA, Blahun OP, Sadkova IV, Tolmachev AA, Moroz YS, Mykhailiuk PK. Chem. Eur. J. 2018; 24: 8343
- 12 Brouwer AJ, Ceylan T, van der Linden T, Liskamp RM. J. Tetrahedron Lett. 2009; 50: 3391
- 13 Chinthakindi PK, Arvidsson PI. Eur. J. Org. Chem. 2018; 3648
- 14 Ballatore C, Huryn DM, Smith AB. ChemMedChem 2013; 8: 385
- 15 Meanwell NA. J. Med. Chem. 2011; 54: 2529
- 16 Rönn R, Sabnis YA, Gossas T, Åkerblom E, HelenaDanielson U, Hallberg A, Johansson A. Bioorg. Med. Chem. 2006; 14: 544
- 17 Scola PM, Wang AX, Good AC, Sun L.-Q, Combrink KD, Campbell JA, Chen J, Tu Y, Sin N, Venables BL, Sit S.-Y, Chen Y, Cocuzza A, Bilder DM, D’Andrea S, Zheng B, Hewawasam P, Ding M, Thuring J, Li J, Hernandez D, Yu F, Falk P, Zhai G, Sheaffer AK, Chen C, Lee MS, Barry D, Knipe JO, Li W, Han Y.-H, Jenkins S, Gesenberg C, Gao Q, Sinz MW, Santone KS, Zvyaga T, Rajamani R, Klei HE, Colonno RJ, Grasela DM, Hughes E, Chien C, Adams S, Levesque PC, Li D, Zhu J, Meanwell NA, McPhee F. J. Med. Chem. 2014; 57: 1708
- 18 Tsuri T, Haga N, Matsui T, Kamata S, Kakushi H, Uchida K. Chem. Pharm. Bull. 1992; 40: 75
- 19 Tsuri T, Matsui T, Haga N, Kamata S, Hagishita S, Takahashi K, Kakushi H, Uchida K, Hatakeyama H, Kurosawa A. Chem. Pharm. Bull. 1992; 40: 85
- 20 Nadin A, Hattotuwagama C, Churcher I. Angew. Chem. Int. Ed. 2012; 51: 1114
- 21 Yang Z, Zhou B, Xu J. Synthesis 2013; 46: 225
- 22 Yang Z, Zheng Y, Xu J. Synlett 2013; 24: 2165
- 23 Yang Z, Xu J. Synthesis 2013; 45: 1675
- 24 Beringer FM, Falk RA. J. Am. Chem. Soc. 1959; 81: 2997
- 25 Uhlenbroek JH, Koopmans MJ, Huisman HO. Recl. Trav. Chim. Pays-Bas 2010; 76: 129
- 26 Favre A, Grugier J, Brans A, Joris B, Marchand-Brynaert J. Tetrahedron 2012; 68: 10818
- 27 Marchand-Brynaert J, Bouchet M, Touillaux R, Beauve C, Fastrez J. Tetrahedron 1996; 52: 5591
- 28 Ghosh AK, Venkateswara Rao K, Yadav ND, Anderson DD, Gavande N, Huang X, Terzyan S, Tang J. J. Med. Chem. 2012; 55: 9195
- 29 Heasley VL, Wade KE, Aucoin TG, Gipe DE, Shellhamer DF. J. Org. Chem. 1983; 48: 1377
- 30 Gala D, Dahanukar VH, Eckert JM, Lucas BS, Schumacher DP, Zavialov IA, Buholzer P, Kubisch P, Mergelsberg I, Scherer D. Org. Process Res. Dev. 2004; 8: 754
- 31 Armarego WL. F, Chai C. Purification of Laboratory Chemicals . Elsevier; Oxford: 2003. 5th ed.
- 32 Phukan P, Chakraborty P, Kataki D. J. Org. Chem. 2006; 71: 7533
- 33 Dewkar GK, Narina SV, Sudalai A. Org. Lett. 2003; 5: 4501
- 34 Kitching W, Olszowy HA, Harvey K. J. Org. Chem. 1982; 47: 1893
- 35 Borsdorf R. J. Prakt. Chem. 1980; 322: 125
- 36 Kumar MA, Naresh M, Rohitha CN, Narender N. Synth. Commun. 2013; 43: 3121
- 37 Puls F, Knölker H.-J. Angew. Chem. Int. Ed. 2018; 57: 1222
- 38 Elangovan S, Topf C, Fischer S, Jiao H, Spannenberg A, Baumann W, Ludwig R, Junge K, Beller M. J. Am. Chem. Soc. 2016; 138: 8809
- 39 Ramadas S, David Krupadanam G. Tetrahedron: Asymmetry 1997; 8: 3059
- 40 Xi X, Chen T, Zhang J.-S, Han L.-B. Chem. Commun. 2018; 54: 1521
- 41 Bernardo JR, Fernandes AC. Green Chem. 2016; 18: 2675
- 42 Calmus L, Corbu A, Cossy J. Adv. Synth. Catal. 2015; 357: 1381