Recent Progress in the Asymmetric Intermolecular Halogenation of Alkenes

Jie Chen; Ling Zhou

doi:10.1055/s-0033-1340787

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(05): 586-595
DOI: 10.1055/s-0033-1340787

short review

Recent Progress in the Asymmetric Intermolecular Halogenation of Alkenes

Jie Chen

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710069, P. R. of China Fax: +86(29)88303915 eMail: zhoul@nwu.edu.cn

,

Ling Zhou*

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710069, P. R. of China Fax: +86(29)88303915 eMail: zhoul@nwu.edu.cn

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

As a long-standing problem in organic chemistry, and a very useful transformation in organic synthesis, the catalytic asymmetric halogenation of alkenes has only recently been reported. New catalysts and novel approaches have been developed for asymmetric halocyclizations. Although mechanism studies indicated the asymmetric intermolecular halogenation of alkenes is more difficult, important breakthroughs have also been achieved. In this review article, the scope, mechanism, and limitations of recently developed catalytic asymmetric intermolecular halogenation of alkenes are described.

1 Introduction

2 Asymmetric Intermolecular Halogenation of Alkenes

2.1 Asymmetric Halogenation of α,β-Unsaturated Compounds

2.2 Asymmetric Halogenation of Allylic Alcohols

2.3 Asymmetric Halogenation of Enecarbamates and Enamides

2.4 Asymmetric Halogenation of Allylic Sulfonamides

2.5 Asymmetric Halogenation of Unfunctionalized Alkenes

3 Summary and Outlook

Key words

alkenes - asymmetric catalysis - enantioselectivity - electrophilic addition - halogenation

Volltext

Referenzen

References

1a Dowle MD, Davies DI. Chem. Soc. Rev. 1979; 8: 171
1b Schmid GH In The Chemistry of Double Bonded Functional Groups . Vol. 2, Part 1. Patai S. Wiley; New York: 1989: 679
1c French AN, Bissmire S, Wirth T. Chem. Soc. Rev. 2004; 33: 354
1d Ruasse M.-F. Adv. Phys. Org. Chem. 1993; 28: 207
1e Ranganathan S, Muraleedharan KM, Vaish NK, Jayaraman N. Tetrahedron 2004; 60: 5273
1f Snyder SA, Treitler DS, Brucks AP. Aldrichimica Acta 2011; 44: 27

For selected reviews on halogenated natural products, see:

2a Gribble GW. Acc. Chem. Res. 1998; 31: 141
2b Paul C, Pohnert G. Nat. Prod. Rep. 2011; 28: 186

3a Reynolds JW. Quart. J., Chem. Soc., London 1851; 3: 111
3b Wislicenus J, Moldenhauer W. Justus Liebigs Ann. Chem. 1868; 146: 175

4a Brown RS, Nagorski RW, Bennet AJ, McClung RE. D, Aarts GH. M, Klobukowski M, McDonald R, Santarsiero BD. J. Am. Chem. Soc. 1994; 116: 2448
4b Neverov AA, Brown RS. J. Org. Chem. 1996; 61: 962
4c Brown RS. Acc. Chem. Res. 1997; 30: 131

5 Denmark SE, Burk MT, Hoover AJ. J. Am. Chem. Soc. 2010; 132: 1232

For selected examples on substrate-controlled asymmetric halogenation of alkenes, see:

6a Terashima S, Jew S.-s. Tetrahedron Lett. 1977; 18: 1005
6b Takano S, Murakata C, Imamura Y. Heterocycles 1981; 16: 1291
6c Tamaru Y, Kawamura S, Bando T, Tanaka K, Hojo M, Yoshida Z. J. Org. Chem. 1988; 53: 5491
6d Llera JM, Lopez JC, Fraser-Reid B. J. Org. Chem. 1990; 55: 2997
6e Shen M, Li C. J. Org. Chem. 2004; 69: 7906
6f Wang YN, Kattuboina A, Ai T, Banerjee D, Li GG. Tetrahedron Lett. 2007; 48: 7894
6g Beshore DC, Smith AB. J. Am. Chem. Soc. 2007; 129: 4148
6h Beshore DC, Smith AB. J. Am. Chem. Soc. 2008; 130: 13778

For selected examples of reagent-controlled asymmetric halogenation of alkenes, see:

7a Kitagawa O, Hanano T, Tanabe K, Shiro M, Taguchi T. J. Chem. Soc., Chem. Commun. 1992; 1005
7b Haas J, Piguel S, Wirth T. Org. Lett. 2002; 4: 297
7c Sakakura A, Ukai A, Ishihara K. Nature (London) 2007; 445: 900
7d Snyder SA, Tang Z.-Y, Gupta R. J. Am. Chem. Soc. 2009; 131: 5744

For selected reviews on asymmetric halogenation of alkenes, see:

8a Castellanos A, Fletcher SP. Chem. Eur. J. 2011; 17: 5766
8b Denmark SE, Kuester WE, Burk MT. Angew. Chem. Int. Ed. 2012; 51: 10938
8c Hennecke U. Chem. Asian J. 2012; 7: 456
8d Snyder SA, Brucks AP In Asymmetric Synthesis II . Christmann M, Bräse S. Wiley-VCH; Weinheim: 2012: 147
8e Tan CK, Yeung Y.-Y. Chem. Commun. 2013; 49: 7985
8f Chemler SR, Bovino MT. ACS Catalysis 2013; 3: 1076

For selected reviews on asymmetric halocyclizations, see:

9a Chen G, Ma S. Angew. Chem. Int. Ed. 2010; 49: 8306
9b Tan CK, Zhou L, Yeung Y.-Y. Synlett 2011; 1335
9c Murai K, Fujioka H. Heterocycles 2013; 87: 763
9d Mendoza AJ, Fananas F, Rodriguez F. Curr. Org. Synth. 2013; 10: 384

For selected examples of asymmetric halolactonizations, see:

10a Wang M, Gao LX, Mai WP, Xia AX, Wang F, Zhang SB. J. Org. Chem. 2004; 69: 2874
10b Ning Z, Jin R, Ding J, Gao L. Synlett 2009; 2291
10c Whitehead DC, Yousefi R, Jaganathan A, Borhan B. J. Am. Chem. Soc. 2010; 132: 3298
10d Zhang W, Zheng S, Liu N, Werness JB, Guzei IA, Tang W. J. Am. Chem. Soc. 2010; 132: 3664
10e Zhou L, Tan CK, Jiang X, Chen F, Yeung Y.-Y. J. Am. Chem. Soc. 2010; 132: 15474
10f Veitch GE, Jacobsen EN. Angew. Chem. Int. Ed. 2010; 49: 7332
10g Murai K, Matsushita T, Nakamura A, Fukushima S, Shimura M, Fujioka H. Angew. Chem. Int. Ed. 2010; 49: 9174
10h Tan CK, Zhou L, Yeung Y.-Y. Org. Lett. 2011; 13: 2738
10i Chen J, Zhou L, Tan CK, Yeung Y.-Y. J. Org. Chem. 2012; 77: 999
10j Yousefi R, Whitehead DC, Mueller JM, Staples RJ, Borhan B. Org. Lett. 2011; 13: 608
10k Jiang X, Tan CK, Zhou L, Yeung Y.-Y. Angew. Chem. Int. Ed. 2012; 51: 7771
10l Dobish MC, Johnston JN. J. Am. Chem. Soc. 2012; 134: 6068
10m Paull DH, Fang C, Donald JR, Pansick AD, Martin SF. J. Am. Chem. Soc. 2012; 134: 11128
10n Zhang W, Liu N, Schienebeck CM, Decloux K, Zheng S, Werness JB, Tang W. Chem. Eur. J. 2012; 18: 7296
10o Wilking M, Mück-Lichtenfeld C, Daniliuc CG, Hennecke U. J. Am. Chem. Soc. 2013; 135: 8133
10p Murai K, Matsushita T, Nakamura A, Hyogo N, Nakajima J, Fujioka H. Org. Lett. 2013; 15: 2526
10q Armstrong A, Braddock DC, Jones AX, Clark S. Tetrahedron Lett. 2013; 54: 7004
10r Yousefi R, Ashtekar KD, Whitehead DC, Jackson JE, Borhan B. J. Am. Chem. Soc. 2013; 135: 14524

For selected examples of asymmetric haloetherifications, see:

11a Kang SH, Lee SB, Park CM. J. Am. Chem. Soc. 2003; 125: 15748
11b Kang SH, Park CM, Lee SB, Kim M. Synlett 2004; 1279
11c Kwon HY, Park CM, Lee SB, Youn J.-H, Kang SH. Chem. Eur. J. 2008; 14: 1023
11d Hennecke U, Müller CH, Fröhlich R. Org. Lett. 2011; 13: 860
11e Huang D, Wang H, Xue F, Guan H, Li L, Peng X, Shi Y. Org. Lett. 2011; 13: 6350
11f Zeng X, Miao C, Wang S, Xia C, Sun W. Chem. Commun. 2013; 49: 2418
11g Tripathi CB, Mukherjee S. Angew. Chem. Int. Ed. 2013; 52: 8450
11h Liu N, Wang H.-Y, Zhang W, Jia Z.-H, Guzei IA, Xu H.-d, Tang W. Chirality 2013; 25: 805

For selected examples of asymmetric halo-N-cyclizations, see:

12a Zhou L, Chen J, Tan CK, Yeung Y.-Y. J. Am. Chem. Soc. 2011; 133: 9164
12b Chen J, Zhou L, Yeung Y.-Y. Org. Biomol. Chem. 2012; 10: 3808
12c Zhou L, Tay DW, Chen J, Leung GY. C, Yeung Y.-Y. Chem. Commun. 2013; 49: 4412
12d Chen F, Tan CK, Yeung Y.-Y. J. Am. Chem. Soc. 2013; 135: 1232
12e Huang D, Liu X, Li L, Cai Y, Liu W, Shi Y. J. Am. Chem. Soc. 2013; 135: 8101
12f Xie W, Jiang G, Liu H, Hu J, Pan X, Zhang H, Wan X, Lai Y, Ma D. Angew. Chem. Int. Ed. 2013; 52: 12924

For selected examples of asymmetric halocyclization of amides, see:

13a Rauniyar V, Lackner AD, Hamilton GL, Toste FD. Science (Washington, D.C.) 2011; 334: 1681
13b Jaganathan A, Garzan A, Whitehead DC, Staples RJ, Borhan B. Angew. Chem. Int. Ed. 2011; 50: 2593
13c Wang Y.-M, Wu J, Hoong C, Rauniyar V, Toste FD. J. Am. Chem. Soc. 2012; 134: 12928
13d Yin Q, You S.-L. Org. Lett. 2013; 15: 4266
13e Jaganathan A, Staples RJ, Borhan B. J. Am. Chem. Soc. 2013; 135: 14806
13f Shunatona HP, Früh N, Wang Y.-M, Rauniyar V, Toste FD. Angew. Chem. Int. Ed. 2013; 52: 7724

For selected examples of halonium ion induced reactions, see:

14a Zhou L, Tan CK, Zhou J, Yeung Y.-Y. J. Am. Chem. Soc. 2010; 132: 10245
14b Zhou L, Chen J, Zhou J, Yeung Y.-Y. Org. Lett. 2011; 13: 5804
14c Zhou L, Zhou J, Tan CK, Chen J, Yeung Y.-Y. Org. Lett. 2011; 13: 2448
14d Chen Z.-M, Zhang Q.-W, Chen Z.-H, Li H, Tu Y.-Q, Zhang F.-M, Tian J.-M. J. Am. Chem. Soc. 2011; 133: 8818
14e Li H, Zhang F.-M, Tu Y.-Q, Zhang Q.-W, Chen Z.-M, Chen Z.-H, Li J. Chem. Sci. 2011; 2: 1839
14f Chen J, Chng S, Zhou L, Yeung Y.-Y. Org. Lett. 2011; 13: 6456
14g Chen Z.-M, Yang B.-M, Chen Z.-H, Zhang Q.-W, Wang M, Tu Y.-Q. Chem. Eur. J. 2012; 18: 12950
14h Romanov-Michailidis F, Guénée L, Alexakis A. Org. Lett. 2013; 15: 5890

For selected examples related to asymmetric halogenations, see:

15a Gustafson JL, Lim D, Miller SJ. Science (Washington, D.C.) 2010; 328: 1251
15b Barrett KT, Miller SJ. J. Am. Chem. Soc. 2013; 135: 2963

For a review, see:

15c Oestreich M. Angew. Chem. Int. Ed. 2005; 44: 2324

16 Cai Y, Liu X, Hui Y, Jiang J, Wang W, Chen W, Lin L, Feng X. Angew. Chem. Int. Ed. 2010; 49: 6160
17 Liu X, Lin L, Feng X. Acc. Chem. Res. 2011; 44: 574
18 Cai Y, Liu X, Jiang J, Chen W, Lin L, Feng X. J. Am. Chem. Soc. 2011; 133: 5636
19 Cai Y, Liu X, Li J, Chen W, Wang W, Lin L, Feng X. Chem. Eur. J. 2011; 17: 14916
20 Cai Y, Liu X, Zhou P, Kuang Y, Lin L, Feng X. Chem. Commun. 2013; 49: 8054
21 Appayee C, Brenner-Moyer SE. Org. Lett. 2010; 12: 3356

22a Sharpless KB, Finn MG In Asymmetric Synthesis . Vol. 5. Morrison JD. Academic; Orlando FL: 1985: 193
22b Pfenninger A. Synthesis 1986; 89
22c Kolb HC, Van Nieuwenhze MS, Sharpless KB. Chem. Rev. 1994; 94: 2483

23 Nicolaou KC, Simmons NL, Ying Y, Heretsch PM, Chen JS. J. Am. Chem. Soc. 2011; 133: 8134

24a Corey EJ, Noe MC. J. Am. Chem. Soc. 1993; 115: 12579
24b Corey EJ, Noe MC. J. Am. Chem. Soc. 1996; 118: 319
24c Corey EJ, Noe MC. J. Am. Chem. Soc. 1996; 118: 11038

25 Hu DX, Shibuya GM, Burns NZ. J. Am. Chem. Soc. 2013; 135: 12960
26 Zhang Y, Xing H, Xie W, Wan X, Lai Y, Ma D. Adv. Synth. Catal. 2013; 355: 68
27 Alix A, Lalli C, Retailleau P, Masson G. J. Am. Chem. Soc. 2012; 134: 10389

For selected reviews, see:

28a Akiyama T. Chem. Rev. 2007; 107: 5744
28b Rueping M, Sugiono E, Schoepke FR. Synlett 2010; 852
28c Terada M. Synthesis 2010; 1929
28d Zamfir A, Schenker S, Freund M, Tsogoeva SB. Org. Biomol. Chem. 2010; 8: 5262
28e Rueping M, Dufour J, Schoepke FR. Green Chem. 2011; 13: 1084
28f Rueping M, Nachtsheim BJ, Ieawsuwan W, Atodiresei I. Angew. Chem. Int. Ed. 2011; 50: 6706
28g Yu J, Shi F, Gong L.-Z. Acc. Chem. Res. 2011; 44: 1156

29 Honjo T, Phipps RJ, Rauniyar V, Toste FD. Angew. Chem. Int. Ed. 2012; 51: 9684
30 Zhang W, Liu N, Schienebeck CM, Zhou X, Izhar II, Guzei IA, Tang W. Chem. Sci. 2013; 4: 2652
31 El-Qisairi A, Hamed O, Henry PM. J. Org. Chem. 1998; 63: 2790
32 El-Qisairi AK, Qaseer HA, Katsigras G, Lorenzi P, Trivedi U, Tracz S, Hartman A, Miller JA, Henry PM. Org. Lett. 2003; 5: 439

33a Tsuji J. Synthesis 1984; 369
33b Sherrington DC. Pure Appl. Chem. 1988; 60: 401
33c Tsuji J In Comprehensive Organic Synthesis . Vol. 7. Trost BM, Fleming I. Pergamon; Oxford: 1991: 551

34 Sakurada I, Yamasaki S, Göttlich R, Iida T, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2000; 122: 1245
35 Adam W, Mock-Knoblauch C, Saha-Möller CR, Herderich M. J. Am. Chem. Soc. 2000; 122: 9685
36 Li G.-x, Fu Q.-q, Zhang X.-m, Jiang J, Tang Z. Tetrahedron: Asymmetry 2012; 23: 245

37a Denmark SE, Burk MT. Org. Lett. 2012; 14: 256
37b Denmark SE, Burk MT. Chirality 2013; in press; DOI 10.1002/chir.22259