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DOI: 10.1055/s-0035-1560406
Recent Progress in Copper-Catalyzed Asymmetric Allylic Substitution Reactions Using Organoboron Nucleophiles
Publication History
Received: 09 December 2015
Accepted after revision: 28 December 2015
Publication Date:
19 February 2016 (online)
Abstract
Recent progress in copper-catalyzed asymmetric allylic substitution reactions with organoboron nucleophiles is reviewed. Wide availability, high functional group compatibility, and mild reaction conditions are the main advantages over conventional highly reactive organometallic nucleophiles. The use of diboron and silylboron reagents for the synthesis of enantioenriched allylboronates and allylsilanes is also included.
1 Introduction
2 Chirality Transfer of Enantioenriched Allylic Substrates with Organoboron Nucleophiles
3 Enantioselective Allylic Substitution of Achiral Substrates with Organoboron Nucleophiles
4 Enantioselective Allylic Substitution of Achiral Substrates with Other Boron-Based Nucleophiles
5 Conclusions
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References
- 1a Oliver S, Evans PA. Synthesis 2013; 45: 3179
- 1b Liu W, Zhao X. Synthesis 2013; 45: 2051
- 1c Sundararaju B, Achard M, Bruneau C. Chem. Soc. Rev. 2012; 41: 4467
- 1d Tosatti P, Nelson A, Marsden SP. Org. Biomol. Chem. 2012; 10: 3147
- 1e Kazmaier U. Transition Metal Catalyzed Enantioselective Allylic Substitution in Organic Synthesis. Springer; Heidelberg: 2012
- 2a Luchaco-Cullis CA, Mizutani H, Murphy KE, Hoveyda AH. Angew. Chem. Int. Ed. 2001; 40: 1456
- 2b Kacprzynski MA, Hoveyda AH. J. Am. Chem. Soc. 2004; 126: 10676
-
2c Van Veldhuizen JJ, Campbell JE, Giudici RE, Hoveyda AH. J. Am. Chem. Soc. 2005; 127: 6877
- 2d Yoshikai N, Miura K, Nakamura E. Adv. Synth. Catal. 2009; 351: 1014
- 2e Jennequin T, Wencel-Delord J, Rix D, Daubignard J, Crévisy C, Mauduit M. Synlett 2010; 1661
- 3a Falciola CA, Alexakis A. Angew. Chem. Int. Ed. 2007; 46: 2619
- 3b Carosi L, Hall DG. Angew. Chem. Int. Ed. 2007; 46: 5913
-
3c Selim KB, Matsumoto Y, Yamada K, Tomioka K. Angew. Chem. Int. Ed. 2009; 48: 8733
- 3d Lölsberg W, Ye S, Schmalz H.-G. Adv. Synth. Catal. 2010; 352: 2023
- 3e Magrez M, Guen YL, Baslé O, Crévisy C, Mauduit M. Chem. Eur. J. 2013; 19: 1199
-
4a Lee Y, Akiyama K, Gillingham DG, Brown MK, Hoveyda AH. J. Am. Chem. Soc. 2008; 130: 446
-
4b Akiyama K, Gao F, Hoveyda AH. Angew. Chem., Int. Ed. 2010; 49: 419
-
4c Gao F, Lee Y, Mandai K, Hoveyda AH. Angew. Chem. Int. Ed. 2010; 49: 8370
-
4d Gao F, McGrath KP, Lee Y, Hoveyda AH. J. Am. Chem. Soc. 2010; 132: 14315
- 4e Dabrowski JA, Gao F, Hoveyda AH. J. Am. Chem. Soc. 2011; 133: 4778
- 5 Ohmiya H, Yokobori U, Makida Y, Sawamura M. J. Am. Chem. Soc. 2010; 132: 2895
- 6 Nagao K, Ohmiya H, Sawamura M. Synthesis 2012; 44: 1535
- 7 Nagao K, Yokobori U, Makida Y, Ohmiya H, Sawamura M. J. Am. Chem. Soc. 2012; 134: 8982
- 8 Yasuda Y, Nagao K, Shido Y, Mori S, Ohmiya H, Sawamura M. Chem. Eur. J. 2015; 21: 9666
- 9 Ohmiya H, Yokokawa N, Sawamura M. Org. Lett. 2010; 12: 2438
- 10 Shintani R, Takatsu K, Takeda M, Hayashi T. Angew. Chem. Int. Ed. 2011; 50: 8656
- 11 Takeda M, Takatsu K, Shintani R, Hayashi T. J. Org. Chem. 2014; 79: 2354
- 12 Jung B, Hoveyda AH. J. Am. Chem. Soc. 2012; 134: 1490
- 13 Gao F, Carr JL, Hoveyda AH. Angew. Chem. Int. Ed. 2012; 51: 6613
- 14 Gao F, Carr JL, Hoveyda AH. J. Am. Chem. Soc. 2014; 136: 2149
- 15 Shi Y, Jung B, Torker S, Hoveyda AH. J. Am. Chem. Soc. 2015; 137: 8948
- 16 Shido Y, Yoshida M, Tanabe M, Ohmiya H, Sawamura M. J. Am. Chem. Soc. 2012; 134: 18573
- 17 Hojoh K, Shido Y, Nagao K, Mori S, Ohmiya H, Sawamura M. Tetrahedron 2015; 71: 6519
- 18 Hojoh K, Shido Y, Ohmiya H, Sawamura M. Angew. Chem. Int. Ed. 2014; 53: 4954
- 19 Ito H, Ito S, Sasaki Y, Matsuura K, Sawamura M. J. Am. Chem. Soc. 2007; 129: 14856
- 20 Ito H, Okura T, Matsuura K, Sawamura M. Angew. Chem. Int. Ed. 2010; 49: 560
- 21 Ito H, Kunii S, Sawamura M. Nat. Chem. 2010; 2: 972
-
22 Guzman-Martinez A, Hoveyda AH. J. Am. Chem. Soc. 2010; 132: 10634
-
23 Park JK, Lackey HH, Ondrusek BA, McQuade DT. J. Am. Chem. Soc. 2011; 133: 2410
- 24 Park JK, McQuade DT. Angew. Chem. Int. Ed. 2012; 51: 2717
- 25 Delvos LB, Oestreich M. Chem. Today 2013; 31 (05) 74
-
26 Delvos LB, Vyas DJ, Oestreich M. Angew. Chem. Int. Ed. 2013; 52: 4650
- 27 Delvos LB, Hensel A, Oestreich M. Synthesis 2014; 46: 2957
- 28 Takeda M, Shintani R, Hayashi T. J. Org. Chem. 2013; 78: 5007
- 29 Delvos LB, Oestreich M. Synthesis 2015; 47: 924
For selected recent reviews, see:
For selected examples, see:
For selected examples, see:
For selected examples, see: