Catalytic Enantioselective Halocyclizations beyond Lactones: Emerging Routes to Enantioenriched Nitrogenous Heterocycles

Chandra Bhushan Tripathi; Santanu Mukherjee

doi:10.1055/s-0033-1340303

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(2): 163-169
DOI: 10.1055/s-0033-1340303

synpacts

Catalytic Enantioselective Halocyclizations beyond Lactones: Emerging Routes to Enantioenriched Nitrogenous Heterocycles

Authors

Chandra Bhushan Tripathi

Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India Fax: +91(80)23600529 eMail: sm@orgchem.iisc.ernet.in
Santanu Mukherjee*

Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India Fax: +91(80)23600529 eMail: sm@orgchem.iisc.ernet.in

Abstract

Alle Artikel dieser Rubrik

Abstract

Electrophilic halogen-induced reactions of unactivated olefins are an important class of transformations, whose catalytic enantioselective variants have surfaced during the past few years as effective means of olefin heterodifunctionalization. This article covers important developments in the area of enantioselective halocyclizations, specifically in the context of the synthesis of nitrogenous heterocycles.

Key words

asymmetric catalysis - halocyclizations - olefins - heterocycles

Volltext

Referenzen

References
1 French AN, Bissmire S, Wirth T. Chem. Soc. Rev. 2004; 33: 354

2a Bougault J. C. R. Hebd. Seances Acad. Sci. 1904; 139: 864
2b Stobbe H, Strigel A, Meyer C. Liebigs Ann. Chem. 1902; 321: 105

3a Laya MS, Banerjee AK, Cabrera EV. Curr. Org. Chem. 2009; 13: 720
3b Ranganathan S, Muraleedharan KM, Vaisha NK, Jayaraman N. Tetrahedron 2004; 60: 5273
3c Dowle MD, Davies DI. Chem. Soc. Rev. 1979; 8: 171

For selected earlier attempts, see:

4a Snyder SA, Treitler DS, Schall A. Tetrahedron 2010; 66: 4796
4b Ning Z, Jin R, Ding J, Gao L. Synlett 2009; 2291
4c Kwon HY, Park CM, Lee SB, Youn J.-H, Kang SH. Chem. Eur. J. 2008; 14: 1023
4d Sakakura A, Ukai A, Ishihara K. Nature 2007; 445: 900
4e Haas J, Bissmire S, Wirth T. Chem. Eur. J. 2005; 11: 5777
4f Wang M, Gao LX, Mai WP, Xia AX, Wang F, Zhang SB. J. Org. Chem. 2004; 69: 2874
4g Kang SH, Park CM, Lee SB, Kim M. Synlett 2004; 1279
4h Kang SH, Lee SB, Park CM. J. Am. Chem. Soc. 2003; 125: 15748
4i Haas J, Piguel S, Wirth T. Org. Lett. 2002; 4: 297
4j Kitagawa O, Hanano T, Tanabe K, Shiro M, Taguchi T. J. Chem. Soc., Chem. Commun. 1992; 1005

For recent reviews, see:

5a Tan CK, Yeung Y.-Y. Chem. Commun. 2013; 49: 7985
5b Chemler SR, Bovino MT. ACS Catal. 2013; 3: 1076
5c Hennecke U. Chem. Asian. J. 2012; 7: 456
5d Castellanos A, Fletcher SP. Chem. Eur. J. 2011; 17: 5766
5e Tan CK, Zhou L, Yeung Y.-Y. Synlett 2011; 1335
5f Snyder SA, Treitler DS, Brucks AP. Aldrichimica Acta 2011; 44: 27

6 For an insightful treatment of this topic with conceptual categorization, see: Denmark SE, Kuester WE, Burk MT. Angew. Chem. Int. Ed. 2012; 51: 10938

7a Murai K, Matsushita T, Nakamura A, Hyogo N, Nakajima J, Fujioka H. Org. Lett. 2013; 15: 2526
7b Paull DH, Fang C, Donald JR, Pansick AD, Martin SF. J. Am. Chem. Soc. 2012; 134: 11128
7c Jiang X, Tan CK, Zhou L, Yeung Y.-Y. Angew. Chem. Int. Ed. 2012; 51: 7771
7d Fang C, Paull DH, Hethcox JC, Shugrue CR, Martin SF. Org. Lett. 2012; 14: 6290
7e Dobish MC, Johnston JN. J. Am. Chem. Soc. 2012; 134: 6068
7f Ikeuchi K, Ido S, Yoshimura S, Asakawa T, Inai M, Hamashima Y, Kan T. Org. Lett. 2012; 14: 6016
7g Murai K, Nakamura A, Matsushita T, Shimura M, Fujioka H. Chem. Eur. J. 2012; 18: 8448
7h Tungen JE, Nolsøe JM. J, Hansen TV. Org. Lett. 2012; 14: 5884
7i Tan CK, Le C, Yeung Y.-Y. Chem. Commun. 2012; 48: 5793
7j Chen J, Zhou L, Tan CK, Yeung Y.-Y. J. Org. Chem. 2012; 77: 999
7k Tan CK, Zhou L, Yeung Y.-Y. Org. Lett. 2011; 13: 2738
7l Yousefi R, Whitehead DC, Mueller JM, Staples RJ, Borhan B. Org. Lett. 2011; 13: 608
7m Zhou L, Tan CK, Jiang X, Chen F, Yeung Y.-Y. J. Am. Chem. Soc. 2010; 132: 15474
7n Murai K, Matsushita T, Nakamura A, Fukushima S, Shimura M, Fujioka H. Angew. Chem. Int. Ed. 2010; 49: 9174
7o Veitch GE, Jacobsen EN. Angew. Chem. Int. Ed. 2010; 49: 7332
7p Whitehead DC, Yousefi R, Jaganathan A, Borhan B. J. Am. Chem. Soc. 2010; 132: 3298

8a Zhang W, Liu N, Schienebeck CM, Decloux K, Zheng S, Werness JB, Tang W. Chem. Eur. J. 2012; 18: 7296
8b Zhang W, Zheng S, Liu N, Werness JB, Guzei IA, Tang W. J. Am. Chem. Soc. 2010; 132: 3664

9 Wilking M, Mück-Lichtenfeld C, Daniliuc CG, Hennecke U. J. Am. Chem. Soc. 2013; 135: 8133

10a Zhao Y, Jiang X, Yeung Y.-Y. Angew. Chem. Int. Ed. 2013; 52: 8597
10b Denmark SE, Burk MT. Org. Lett. 2012; 14: 256
10c Hennecke U, Müller CH, Fröhlich R. Org. Lett. 2011; 13: 860
10d Wilkinson SC, Lozano O, Schuler M, Pacheco MC, Salmon R, Gouverneur V. Angew. Chem. Int. Ed. 2009; 48: 7083

11 Zhou L, Chen J, Tan CK, Yeung Y.-Y. J. Am. Chem. Soc. 2011; 133: 9164
12 Chen J, Zhou L, Yeung Y.-Y. Org. Biomol. Chem. 2012; 10: 3808
13 Zhou L, Tay DW, Chen J, Leung GY. C, Yeung Y.-Y. Chem. Commun. 2013; 49: 4412
14 Huang D, Wang H, Xue F, Guan H, Li L, Peng X, Shi Y. Org. Lett. 2011; 13: 6350
15 Chen F, Tan CK, Yeung Y.-Y. J. Am. Chem. Soc. 2013; 135: 1232

16a Hu DX, Shibuya GM, Burns NZ. J. Am. Chem. Soc. 2013; 135: 12960
16b Miles DH, Veguillas M, Toste FD. Chem. Sci. 2013; 4: 3427
16c Cochrane NA, Nguyen H, Gagne MR. J. Am. Chem. Soc. 2013; 135: 628
16d Alix A, Lalli C, Retailleau P, Masson G. J. Am. Chem. Soc. 2012; 134: 10389
16e Lee HJ, Kim DY. Tetrahedron Lett. 2012; 53: 6984
16f El-Qisairi A, Hamed O, Henry PM. J. Org. Chem. 1998; 63: 2790

For halofunctionalization of α,β-unsaturated carbonyls, see refs. 4c, 4h and:

16g Cai Y, Liu X, Zhou P, Kuang Y, Lin L, Feng X. Chem. Commun. 2013; 49: 8054
16h Cai Y, Liu X, Li J, Chen W, Wang W, Lin L, Feng X. Chem. Eur. J. 2011; 17: 14916
16i Cai Y, Liu X, Jiang J, Chen W, Lin L, Feng X. J. Am. Chem. Soc. 2011; 133: 5636
16j Cai Y, Liu X, Hui Y, Jiang J, Wang W, Chen W, Lin L, Feng X. Angew. Chem. Int. Ed. 2010; 49: 6160

17 Huang D, Liu X, Li L, Cai Y, Liu W, Shi Y. J. Am. Chem. Soc. 2013; 135: 8101
18 Brindle CS, Yeung CS, Jacobsen EN. Chem. Sci. 2013; 4: 2100
19 Jaganathan A, Garzan A, Whitehead DC, Staples RJ, Borhan B. Angew. Chem. Int. Ed. 2011; 50: 2593
20 Garzan A, Jaganathan A, Marzijarani NS, Yousefi R, Whitehead DC, Jackson JE, Borhan B. Chem. Eur. J. 2013; 19: 9015
21 Yin Q, You S.-L. Org. Lett. 2013; 15: 4266
22 Lozano O, Blessley G, del Campo TM, Thompson AL, Giuffredi GT, Bettati M, Walker M, Borman R, Gouverneur V. Angew. Chem. Int. Ed. 2011; 50: 8105
23 Rauniyar V, Lackner AD, Hamilton GL, Toste FD. Science 2011; 334: 1681
24 Wang Y.-M, Wu J, Hoong C, Rauniyar V, Toste FD. J. Am. Chem. Soc. 2012; 134: 12928
25 Shunatona HP, Früh N, Wang Y.-M, Rauniyar V, Toste FD. Angew. Chem. Int. Ed. 2013; 52: 7724
26 For a nonasymmetric bromoetherification of β,γ-unsaturated oximes, see: Mosher MD, Norman AL, Shurrush KA. Tetrahedron Lett. 2009; 50: 5647
27 Tripathi CB, Mukherjee S. Angew. Chem. Int. Ed. 2013; 52: 8450

28a Castellano S, Kuck D, Viviano M, Yoo J, López-Vallejo F, Conti P, Tamborini L, Pinto A, Medina-Franco JL, Sbardella G. J. Med. Chem. 2011; 54: 7663
28b Poutiainen PK, Venäläinen TA, Peräkylä M, Matilainen JM, Väisänen S, Honkakoski P, Laatikainen R, Pulkkinen JT. Bioorg. Med. Chem. 2010; 18: 3437

29 Namboothiri IN. N, Rastogi N. Top. Heterocycl. Chem. 2008; 12: 1
30 For a nonasymmetric route to Δ²-isoxazolines containing a quaternary stereogenic center, see: Zhu M.-K, Zhao J.-F, Loh T.-P. J. Am. Chem. Soc. 2010; 132: 6284
31 Denmark SE, Burk MT. Proc. Natl. Acad. Sci. U.S.A. 2010; 107: 20655
32 Tripathi CB, Mukherjee S. J. Org. Chem. 2012; 77: 1592

For reviews on anion-binding catalysis, see:

33a Brak K, Jacobsen EN. Angew. Chem. Int. Ed. 2013; 52: 534
33b Mahlau M, List B. Angew. Chem. Int. Ed. 2013; 52: 518

For a recent report on enantioselective carbosulfenylation, see:

34a Denmark SE, Jaunet A. J. Am. Chem. Soc. 2013; 135: 6419

For related halogen-induced semipinacol rearrangements involving unactivated olefins, see:

34b Romanov-Michailidis F, Guénéé L, Alexakis A. Angew. Chem. Int. Ed. 2013; 52: 9266
34c Müller CH, Wilking M, Rühlmann A, Wibbeling B, Hennecke U. Synlett 2011; 2043
34d Li H, Zhang F.-M, Tu Y.-Q, Zhang Q.-W, Chen Z.-M, Chen Z.-H, Li J. Chem. Sci. 2011; 2: 1839 ; For a stoichiometric example, see ref. 4d

For the sole example of intermolecular halofunctionalization of unactivated olefins, see:

35a Zhang W, Liu N, Schienebeck CM, Zhou X, Izhar II, Guzei IA, Tang W. Chem. Sci. 2013; 4: 2652

For some related transformations, see refs. 16a, 16f and:

35b Nicolaou KC, Simmons NL, Ying Y, Heretsch PM, Chen JS. J. Am. Chem. Soc. 2011; 133: 8134
35c El-Qisairi AK, Qaseer HA, Katsigras G, Lorenzi P, Trivedi U, Tracz S, Hartman A, Miller JA, Henry PM. Org. Lett. 2003; 5: 439
35d Sakurada I, Yamasaki S, Göttlich R, Iida T, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2000; 122: 1245

36 For a different approach to the halocyclization of monosubstituted olefins, see: Bovino MT, Chemler SR. Angew. Chem. Int. Ed. 2012; 51: 3923