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Synthesis 2013; 45(15): 2125-2133
DOI: 10.1055/s-0033-1338418
DOI: 10.1055/s-0033-1338418
special topic
Rhodium-Catalyzed Highly Enantioselective Addition of Arylboronic Acids to Cyclic Aldimines: Practical Asymmetric Synthesis of Cyclic Sulfamidates
Further Information
Publication History
Received: 21 February 2013
Accepted after revision: 25 March 2013
Publication Date:
08 May 2013 (online)
Abstract
A highly efficient asymmetric arylation of cyclic N-sulfonyl aldimines with arylboronic acids catalyzed by a rhodium/ sulfur–olefin ligand complex under mild conditions is described. A wide range 4-aryl-3,4-dihydro-1,2,3-benzoxathiazine 2,2-dioxides were obtained in extremely high yields (93–99%) and high enantiomeric purities (97–99% ee).
Key words
asymmetric catalysis - cyclization - arylation - rhodium - boron - ligands - sulfamidates - heterocyclesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1a Liu YG, Xiao WB, Wong MK, Che CM. Org. Lett. 2007; 9: 4107
- 1b Alig B, Müller KH, Franken E.-M, Görgens U, Voerste A. WO2010072310, 2010
- 1c Kim SJ, Jung MH, Yoo KH, Cho JH, Oh CH. Bioorg. Med. Chem. Lett. 2008; 18: 5815
- 1d Kim SJ, Park HB, Lee JS, Jo NH, Yoo KH, Baek D, Kang B.-w, Cho JH, Oh CH. Eur. J. Med. Chem. 2007; 42: 1176
- 1e Petry S, Baringhaus KH, Hölder S, Mueller G. WO2002011722, 2002
- 2a Meleńdez RE, Lubell WD. Tetrahedron 2003; 59: 2581
- 2b Brodsky BH, Du Bois J. J. Am. Chem. Soc. 2005; 127: 15391
- 2c Ni C, Liu J, Zhang L, Hu J. Angew. Chem. Int. Ed. 2007; 46: 786
- 2d Bower JF, Szeto P, Gallagher T. Org. Lett. 2007; 9: 3283
- 2e Rönnholm P, Södergren M, Hilmersson G. Org. Lett. 2007; 9: 3781
- 2f Bower JF, Švenda J, Williams AJ, Charmant JP. H, Lawrence RM, Szeto P, Gallagher T. Org. Lett. 2004; 6: 4727
- 2g Cohen SB, Halcomb RL. J. Am. Chem. Soc. 2002; 124: 2534
- 2h Bower JF, Szeto P, Gallagher T. Org. Lett. 2007; 9: 4909
- 3a Posakony JJ, Tewson TJ. Synthesis 2002; 766
- 3b Andersen KK, Bray DD, Chumpradit S, Clark ME, Habgood GJ, Hubbard CD, Young KM. J. Org. Chem. 1991; 56: 6508
- 3c Aguilera B, Fernández-Mayoralas A. Chem. Commun. 1996; 127
- 3d Aguilera B, Fernández-Mayoralas A, Jaramillo C. Tetrahedron 1997; 53: 5863
- 3e Lyle TA, Magill CA, Pitzenberger SM. J. Am. Chem. Soc. 1987; 109: 7890
- 3f Alker D, Doyle KJ, Harwood LM, McGregor A. Tetrahedron: Asymmetry 1990; 1: 877
- 3g Nicolaou KC, Snyder SA, Longbottom DA, Nalbandian AZ, Huang X. Chem. Eur. J. 2004; 10: 5581
- 3h Nicolaou KC, Huang X, Snyder SA, Rao PB, Bella M, Reddy MV. Angew. Chem. Int. Ed. 2002; 41: 834
- 4a Espino CG, Wehn PM, Chow J, Du Bois J. J. Am. Chem. Soc. 2001; 123: 6935
- 4b Wehn PM, Du Bois J. J. Am. Chem. Soc. 2002; 124: 12950
- 4c Fleming JJ, Fiori KW, Du Bois J. J. Am. Chem. Soc. 2003; 125: 2028
- 5a Liang J.-L, Yuan S.-X, Huang J.-S, Yu W.-Y, Che C.-M. Angew. Chem. Int. Ed. 2002; 41: 3465
- 5b Liang J.-L, Yuan S.-X, Huang J.-S, Che C.-M. J. Org. Chem. 2004; 69: 3610
- 5c Zhang J, Chan PW. H, Che C.-M. Tetrahedron Lett. 2005; 35: 5403
- 5d Fruit C, Müller P. Tetrahedron: Asymmetry 2004; 15: 1019
- 6a Barman DN, Nicholas KM. Eur. J. Org. Chem. 2011; 908
- 6b Duran F, Leman L, Ghini A, Burton G, Dauban P, Dodd RH. Org. Lett. 2002; 4: 2481
- 7 Wang Y.-Q, Yu C.-B, Wang D.-W, Wang X.-B, Zhou Y.-G. Org. Lett. 2008; 10: 2071
- 8a Luo Y.-F, Carnell AJ, Lam HW. Angew. Chem. Int. Ed. 2012; 51: 6762
- 8b Luo Y.-F, Hepburn HB, Chotsaeng N, Lam HW. Angew. Chem. Int. Ed. 2012; 51: 8309
- 8c Nishimura T, Noishiki A, Tsui GC, Hayashi T. J. Am. Chem. Soc. 2012; 134: 5056
- 9 Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine. Hall DG. Wiley-VCH; Weinheim: 2005
- 10a Jin S.-S, Wang H, Xu M.-H. Chem. Commun. 2011; 47: 7230
- 10b Qi W.-Y, Zhu T.-S, Xu M.-H. Org. Lett. 2011; 13: 3410
- 10c Jin S.-S, Wang H, Zhu T.-S, Xu M.-H. Org. Biomol. Chem. 2012; 10: 1764
- 10d Zhu T.-S, Jin S.-S, Xu M.-H. Angew. Chem. Int. Ed. 2012; 51: 780
- 10e Wang H, Zhu T.-S, Xu M.-H. Org. Biomol. Chem. 2012; 10: 9158
- 10f Zhu T.-S, Chen J.-P, Xu M.-H. Chem. Eur. J. 2013; 19: 865
- 10g Wang H, Jiang T, Xu M.-H. J. Am. Chem. Soc. 2013; 135: 971
- 11a Thaler T, Guo L.-N, Steib AK, Raducan M, Karaghiosoff K, Mayer P, Knochel P. Org. Lett. 2011; 13: 3182
- 11b Feng X, Wang Y, Wei B, Yang J, Du H. Org. Lett. 2011; 13: 3300
- 11c Chen G, Gui J, Li L, Liao J. Angew. Chem. Int. Ed. 2011; 50: 7681
- 11d Xue F, Li X, Wan B. J. Org. Chem. 2011; 76: 7256
- 11e Khiar N, Salvador A, Chelouan A, Alcudia A, Fernández I. Org. Biomol. Chem. 2012; 10: 2366
- 12 Crystallographic data for compound (R)-3z have been deposited with the accession number CCDC 92598, and can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk; web site: www.ccdc.cam.ac.uk/conts/retrieving.html.
- 13a Hayashi T, Ueyama K, Tokunaga N, Yoshida K. J. Am. Chem. Soc. 2003; 125: 11508
- 13b Fagnou K, Lautens M. Chem. Rev. 2003; 103: 169
- 13c Hayashi T, Yamasaki K. Chem. Rev. 2003; 103: 2829
- 14a Kantchev EA. B. Chem. Commun. 2011; 47: 10969
- 14b Gosiewska S, Raskatov JA, Shintani R, Hayashi T, Brown JM. Chem. Eur. J. 2012; 18: 80
- 14c Luo Y, Berry NG, Carnell AJ. Chem. Commun. 2012; 48: 3279
For a review, see:
For selected examples, see:
For examples of intramolecular copper-catalyzed amination and aziridination, see:
For selected recent reports on chiral sulfur–olefin ligands by other groups, see:
For recent related computational studies, see: