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DOI: 10.1055/s-0033-1340787
Recent Progress in the Asymmetric Intermolecular Halogenation of Alkenes
Publikationsverlauf
Received: 22. Dezember 2013
Accepted after revision: 20. Januar 2014
Publikationsdatum:
31. Januar 2014 (online)
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
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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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
For selected reviews on halogenated natural products, see:
For selected examples on substrate-controlled asymmetric halogenation of alkenes, see:
For selected examples of reagent-controlled asymmetric halogenation of alkenes, see:
For selected reviews on asymmetric halogenation of alkenes, see:
For selected reviews on asymmetric halocyclizations, see:
For selected examples of asymmetric halolactonizations, see:
For selected examples of asymmetric haloetherifications, see:
For selected examples of asymmetric halo-N-cyclizations, see:
For selected examples of asymmetric halocyclization of amides, see:
For selected examples of halonium ion induced reactions, see:
For selected examples related to asymmetric halogenations, see:
For a review, see:
For selected reviews, see: