Palladium-Catalyzed Decarboxylative [4+2] Cycloaddition of Vinyl Benzoxazinanones with Cyclic N-Sulfimines: Stereoselective Synthesis­ of Benzosulfamidate-Fused Tetrahydroquinazolines

Dasom Mun; Eunjin Kim; Sung-Gon Kim

doi:10.1055/s-0037-1610685

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(11): 2359-2370
DOI: 10.1055/s-0037-1610685

paper

Palladium-Catalyzed Decarboxylative [4+2] Cycloaddition of Vinyl Benzoxazinanones with Cyclic N-Sulfimines: Stereoselective Synthesis of Benzosulfamidate-Fused Tetrahydroquinazolines

Dasom Mun

,

Eunjin Kim

,

Sung-Gon Kim*

Department of Chemistry, Kyonggi University, 154-42 Gwanggyosan-ro, Yeongtong-gu, Suwon 16227, Republic of Korea eMail: sgkim123@kyonggi.ac.kr

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

Methods for the catalytic synthesis of highly functionalized benzosulfamidate-fused tetrahydroquinazolines are presented. The decarboxylative [4+2] cycloaddition of vinyl benzoxazinanones with benzoxathiazine 2,2-dioxides catalyzed by Pd(PPh₃)₄ affords fused-tetrahydroquinazolines with high diastereoselectivities. Alternatively, catalytic asymmetric [4+2] cycloaddition employing a chiral palladium-containing phosphoramidite ligand provides optically enriched benzosulfamidate-fused tetrahydroquinazolines in good yields and with excellent diastereoselectivities and enantioselectivities.

Key words

asymmetric catalysis - cycloaddition - vinyl benzoxazinanones - cyclic N-sulfimines - palladium

Volltext

Referenzen

References

1a Heterocycles in Natural Product Synthesis . Majumdar KC, Chattopadhyay SK. Wiley-VCH; Weinheim: 2011
1b Baumann M, Baxendale IR, Ley SV, Nikbin N. Beilstein J. Org. Chem. 2011; 7: 442
1c Baumann M, Baxendale IR. Beilstein J. Org. Chem. 2013; 9: 2265

2 Verdel BM, Souverein PC, Egberts AC. G, Leufkens HG. M. Ann. Pharm. 2006; 40: 1040 ; and references cited therein
3 Corbett JW, Ko SS, Rodgers JD, Gearhart LA, Magnus NA, Bacheler LT, Diamond S, Jeffrey S, Klabe RM, Cordova BC, Garber S, Logue K, Trainor GL, Anderson PS, Erickson-Viitanen SK. J. Med. Chem. 2000; 43: 2019

4a Rasul A, Yu B, Zhong L, Khan M, Yang H, Ma T. Oncol. Rep. 2012; 27: 1481
4b Kobayashi Y, Nakano Y, Kizaki M, Hoshikuma K, Yokoo Y, Kamiya T. Planta Med. 2001; 67: 628

5a Cheng X, Vellalath S, Goddard R, List B. J. Am. Chem. Soc. 2008; 130: 15786
5b Rueping M, Antonchick AP, Sugiono E, Grenader K. Angew. Chem. Int. Ed. 2009; 48: 908
5c Prakash M, Kesavan V. Org. Lett. 2012; 14: 1896
5d Cheng D.-J, Tian Y, Tian S.-K. Adv. Synth. Catal. 2012; 354: 995
5e Prakash M, Jayakumar S, Kesavan V. Synthesis 2013; 45: 2265
5f Huang D, Li X, Xu F, Li L, Lin X. ACS Catal. 2013; 3: 2244
5g Armstrong RJ, D’Ascenzio M, Smith MD. Synlett 2016; 27: 6
5h Sui Y, Cui P, Liu S, Zhou Y, Du P, Zhou H. Eur. J. Org. Chem. 2018; 215

6a He Y.-P, Du Y.-L, Luo S.-W, Gong L.-Z. Tetrahedron Lett. 2011; 52: 7064
6b He Y.-P, Wu H, Chen D.-F, Yu J, Gong L.-Z. Chem. Eur. J. 2013; 19: 5232
6c Wang YN, Wang BC, Zhang MM, Gao XW, Li TR, Lu L.-Q, Xiao WJ. Org. Lett. 2017; 19: 4094

7 Sim J.-T, Kim H, Kim S.-G. Tetrahedron Lett. 2016; 57: 5907

8a Wang C, Tunge JA. J. Am. Chem. Soc. 2008; 130: 8118
8b Li T.-R, Tan F, Lu L.-Q, Wei Y, Wang YN, Liu Y.-Y, Yang Q.-Q, Chen J.-R, Shi D.-Q, Xiao W.-J. Nat. Commun. 2014; 5: 5500
8c Wei Y, Lu L.-Q, Li T.-R, Feng B, Wang Q, Xiao W.-J, Alper H. Angew. Chem. Int. Ed. 2016; 55: 2200
8d Guo C, Fleige M, Janssen-Müller D, Daniliuc CG, Glorius F. J. Am. Chem. Soc. 2016; 138: 7840
8e Leth LA, Glaus F, Meazza M, Fu L, Thøgersen KM, Bitsch EA, Jørgensen KA. Angew. Chem. Int. Ed. 2016; 55: 12272
8f Mei G.-J, Bian C.-Y, Li G.-H, Xu S.-L, Zheng W.-Q, Shi F. Org. Lett. 2017; 19: 3219
8g Guo C, Janssen-Müller D, Fleige M, Lerchen A, Daniliuc CG, Glorius F. J. Am. Chem. Soc. 2017; 139: 4443

9 During the preparation of this manuscript, a palladium-catalyzed enantioselective [4+2] cycloaddition reaction of vinyl benzoxazinones with sulfamate-derived cyclic imines was reported, see: Wang C, Li Y, Wu Y, Wang Q, Shi W, Yuan C, Zhou L, Xiao Y, Guo H. Org. Lett. 2018; 20: 2880

10a Winum J.-Y, Scozzafava A, Montero J.-L, Supuran CT. Med. Res. Rev. 2005; 25: 186
10b Winum J.-Y, Scozzafava A, Montero J.-L, Supuran CT. Expert Opin. Ther. Pat. 2006; 16: 27
10c Woo LW. L, Purohit A, Potter BV. L. Mol. Cell. Endocrinol. 2011; 340: 175
10d Williams SJ. Expert Opin. Ther. Pat. 2013; 23: 79
10e Bower JF, Rujirawanich J, Gallagher T. Org. Biomol. Chem. 2010; 8: 1505
10f Baig RB. N, Nadagouda MN, Varma RS. Aldrichimica Acta 2015; 48: 71

For selected examples, see:

11a Parthasarathy K, Azcargorta AR, Cheng Y, Bolm C. Org. Lett. 2014; 16: 2538
11b Zhang H.-X, Nie J, Cai H, Ma J.-A. Org. Lett. 2014; 16: 2542
11c Jiang C, Lu Y, Hayashi T. Angew. Chem. Int. Ed. 2014; 53: 9936
11d Jiang T, Wang Z, Xu M.-H. Org. Lett. 2015; 17: 528
11e Gigant N, Drège E, Retailleau P, Joseph D. Chem. Eur. J. 2015; 21: 15544
11f Lai B.-N, Qiu J.-F, Zhang H.-X, Nie J, Ma J.-A. Org. Lett. 2016; 18: 520
11g De Munck L, Vila C, Muñoz MC, Pedro JR. Chem. Eur. J. 2016; 22: 17590
11h Quan M, Tang L, Shen J, Yang G, Zhang W. Chem. Commun. 2017; 53: 609
11i De Munck L, Monleón A, Vila C, Pedro JR. Adv. Synth. Catal. 2017; 359: 1582
11j Wu Y, Yuan C, Wang C, Mao B, Jia H, Gao X, Liao J, Jiang F, Zhou L, Wang Q, Guo H. Org. Lett. 2017; 19: 6268
11k Jin J.-H, Wang H, Yang Z.-T, Yang W.-L, Tang W, Deng W.-P. Org. Lett. 2018; 20: 104

12a Kim H, Kim Y, Kim S.-G. J. Org. Chem. 2017; 82: 8179
12b Lee SG, Kim S.-G. RSC Adv. 2017; 7: 34283

For selected reviews on chiral phosphoramidite ligands, see:

13a Teichert J, Feringa BL. Angew. Chem. Int. Ed. 2010; 49: 2486
13b Fu W, Tang W. ACS Catal. 2016; 6: 4814

Zusatzmaterial

Supporting Information

Palladium-Catalyzed Decarboxylative [4+2] Cycloaddition of Vinyl Benzoxazinanones with Cyclic N-Sulfimines: Stereoselective Synthesis­ of Benzosulfamidate-Fused Tetrahydroquinazolines

Palladium-Catalyzed Decarboxylative [4+2] Cycloaddition of Vinyl Benzoxazinanones with Cyclic N-Sulfimines: Stereoselective Synthesis of Benzosulfamidate-Fused Tetrahydroquinazolines