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Synthesis 2016; 48(23): 4038-4049
DOI: 10.1055/s-0036-1589457
DOI: 10.1055/s-0036-1589457
short review
Recent Advances in the Asymmetric Nozaki–Hiyama–Kishi Reaction
Weitere Informationen
Publikationsverlauf
Received: 18. Mai 2016
Accepted after revision: 01. Juli 2016
Publikationsdatum:
24. August 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201623/lookinside/thumbnails/ss-2016-h0362-sr_10-1055_s-0036-1589457-1.jpg)
Abstract
This review will survey recent developments in the area of the catalytic asymmetric Nozaki–Hiyama–Kishi reaction. The content will be classified according to reaction type as follows: asymmetric allylation, asymmetric propargylation, asymmetric alkynylation, asymmetric vinylation, and asymmetric alkylation.
1 Introduction
2 Asymmetric Allylation
3 Asymmetric Propargylation and Asymmetric Homoallenylation
4 Asymmetric Alkynylation
5 Asymmetric Vinylation and Arylation
6 Asymmetric Alkylation
7 Intramolecular Nozaki–Hiyama–Kishi Reaction
8 Conclusion and Perspectives
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References
-
1a Okude Y, Hirano S, Hiyama T, Nozaki H. J. Am. Chem. Soc. 1977; 99: 3179
- 1b Takai K, Kimura K, Kuroda T, Hiyama T, Nozaki H. Tetrahedron Lett. 1983; 24: 5281
-
1c Jin H, Uenishi J.-I, Christ WJ, Kishi Y. J. Am. Chem. Soc. 1986; 108: 5644
-
1d Takai K, Tagashira M, Kuroda T, Oshima K, Utimoto K, Nozaki H. J. Am. Chem. Soc. 1986; 108: 6048
-
2a Fürstner A, Shi N. J. Am. Chem. Soc. 1996; 118: 12349
-
2b Fürstner A, Shi N. J. Am. Chem. Soc. 1996; 118: 2533
- 3 Hargaden GC, Guiry PG In Stereoselective Synthesis of Drugs and Natural Products . Vol. 1. Andrushko V, Andrushko N. Wiley-VCH; Weinheim: 2013. Chap. 12, 347
- 4 Hargaden GC, Guiry PJ. Adv. Synth. Catal. 2007; 349: 2407
- 5 Hargaden GC, Guiry PG In Innovative Catalysis in Organic Synthesis . Andersson P. Wiley-VCH; Weinheim: 2012: 279
- 6 Yus M, Gonzalez-Gomez JC, Foubelo F. Chem. Rev. 2011; 111: 7774
- 7 Chen C, Tagami K, Kishi Y. J. Org. Chem. 1995; 60: 5386
- 8 Sugimoto K, Aoyagi S, Kibayashi C. J. Org. Chem. 1997; 62: 2322
- 9 Bandini M, Cozzi PG, Melchiorre P, Umani-Ronchi A. Angew. Chem. Int. Ed. 1999; 38: 3357
- 10 Bandini M, Cozzi PG, Licciulli S, Umani-Ronchi A. Synthesis 2004; 409
- 11 Berkessel A, Menche D, Sklorz CA, Schroder M, Paterson I. Angew. Chem. Int. Ed. 2003; 42: 1032
- 12 White JD, Shaw S. Org. Lett. 2011; 13: 2488
- 13 Kurosu M, Lin M.-H, Kishi Y. J. Am. Chem. Soc. 2004; 126: 12248
- 14 Zhang Z, Huang J, Ma B, Kishi Y. Org. Lett. 2008; 10: 3073
- 15 Xia G, Yamamoto H. J. Am. Chem. Soc. 2006; 128: 2554
- 16 Inoue M, Suzuki T, Nakada M. J. Am. Chem. Soc. 2003; 125: 1140
- 17 Inoue M, Suzuki T, Nakada M. Synlett 2003; 570
- 18 Deng Q.-H, Wadepohl H, Gade LH. Chem. Eur. J. 2011; 17: 14922
- 19 McManus HA, Cozzi PG, Guiry PJ. Adv. Synth. Catal. 2006; 348: 551
- 20 Hargaden GC, McManus HA, Cozzi PG, Guiry PJ. Org. Biomol. Chem. 2007; 5: 763
- 21 Hargaden GC, O’Sullivan TP, Guiry PJ. Org. Biomol. Chem. 2008; 6: 562
- 22 Deng Q.-H, Melen RL, Gade LH. Acc. Chem. Res. 2014; 47: 3162
- 23 Inoue M, Suzuki T, Kinoshita A, Nakada M. Chem. Rec. 2008; 8: 169
- 24 Chen W, Yang Q, Zhou T, Tian Q, Zhang G. Org. Lett. 2015; 17: 5236
- 25 Tian Q, Bai J, Chen B, Zhang G. Org. Lett. 2016; 18: 1828
- 26 Lee J.-Y, Miller JJ, Hamilton SS, Sigman MS. Org. Lett. 2005; 7: 1837
- 27 Miller JJ, Sigman MS. J. Am. Chem. Soc. 2007; 129: 2752
- 28 Bandini M, Cozzi PG, Umani-Ronchi A. Polyhedron 2000; 19: 537
- 29 Inoue M, Nakada M. Org. Lett. 2004; 6: 2977
- 30 Usanov DL, Yamamoto H. Angew. Chem. Int. Ed. 2010; 49: 8169
- 31 Xia G, Yamamoto H. J. Am. Chem. Soc. 2007; 129: 496
- 32 Coeffard V, Aylward M, Guiry PJ. Angew. Chem. Int. Ed. 2009; 48: 9152
- 33 Liu S, Kim JT, Dong C.-G, Kishi Y. Org. Lett. 2009; 11: 4520
- 34 Harper KC, Sigman MS. Science 2011; 333: 1875
- 35 Usanov DL, Yamamoto H. J. Am. Chem. Soc. 2011; 133: 1286
- 36a Choi H.-w, Demeke D, Kang F.-A, Kishi Y, Nakajima K, Nowak P, Wan Z.-K, Xie C. Pure Appl. Chem. 2003; 75: 1
- 36b Liu X, Li X, Chen Y, Hu Y, Kishi Y. J. Am. Chem. Soc. 2012; 134: 6136
- 37 Choi H, Nakajima K, Demeke D, Kang F.-A, Jun H.-S, Wan Z.-K, Kishi Y. Org. Lett. 2002; 4: 4435
- 38 Kim D.-S, Dong C.-G, Kim JT, Guo H, Huang J, Tiseni PS, Kishi Y. J. Am. Chem. Soc. 2009; 131: 15636
- 39 Guo H, Dong C.-G, Kim D.-S, Urabe D, Wang J, Kim JT, Liu X, Sasaki T, Kishi Y. J. Am. Chem. Soc. 2009; 131: 15387
- 40 Namba K, Kishi Y. J. Am. Chem. Soc. 2005; 127: 15382
- 41a Nishikawa T, Shibuya S, Hosokawa S, Isobe M. Synlett 1994; 485
- 41b Wang J, DeClercq PJ. Angew. Chem., Int. Ed. Engl. 1995; 34: 1749
- 42 Guella G, Pietra FJ. J. Chem. Soc., Chem. Commun. 1993; 1539
-
43 Williams DR, Walsh MJ, Miller NA. J. Am. Chem. Soc. 2009; 131: 9038
- 44 Mohapatra DK, Das PP, Pattanayak MR, Gayatri G, Sastry GN, Yadav JS. Eur. J. Org. Chem. 2010; 4775
- 45 Pettit GR, Cichacz ZA, Gao F, Boyd MR, Schmidt JM. J. Chem. Soc., Chem. Commun. 1994; 1111
-
46 Zhu W, Jiménez M, Jung W.-H, Camarco DP, Balachandran R, Vogt A, Day BW, Curran DP. J. Am. Chem. Soc. 2010; 132: 9175
- 47 Baker TM, Edmonds DJ, Hamilton D, O’Brien CJ, Procter DJ. Angew. Chem. Int. Ed. 2008; 47: 5631
- 48 Pospisil J, Muller C, Fürstner A. Chem. Eur. J. 2009; 15: 5956