Abstract
Asymmetric β-borylation (conjugate borylation) of α,β-unsaturated acceptors allows the efficient synthesis of chiral organoboron compounds bearing extra functional groups. In the last 8 years, impressive progress has been made regarding this reaction since the first asymmetric report. While copper catalysis has dominated the field of asymmetric borylation due to its high reactivity and selectivity, various metal-catalyzed and metal-free methods have also been developed. The present chapter covers recent developments in asymmetric borylation of α,β-unsaturated compounds while focusing on the substrate scope and enantioselectivity of each catalytic system. In addition, recent achievements of asymmetric borylation conducted in water are briefly presented.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Lawson YG, Lesley MJG, Marder TB, Norman NC, Rice CG (1997) Chem Commun 2051
Ito H, Yamanaka H, Tateiwa J, Hosomi A (2000) Tetrahedron Lett 41:6821
Takahashi K, Ishiyama T, Miyaura N (2000) Chem Lett 982
Kabalka GW, Das BC, Das S (2002) Tetrahedron Lett 43:2323
Mun S, Lee JE, Yun J (2006) Org Lett 8:4887
Lee JE, Yun J (2008) Angew Chem Int Ed 47:145
Bonet A, Gulyás H, Fernández E (2010) Angew Chem Int Ed 49:5130
Wu H, Radomkit S, O’Brien JM, Hoveyda AH (2012) J Am Chem Soc 134:8277
Takahashi K, Ishiyama T, Miyaura N (2001) J Orgmetal Chem 625:47
Dang L, Lin Z, Marder TB (2008) Organometallics 27:4443
Sim HS, Feng X, Yun J (2009) Chem Eur J 15:1939
Chea H, Sim HS, Yun J (2009) Adv Synth Catal 351:855
Herrmann WA (2002) Angew Chem Int Ed 41:1290
Díez-González S, Marion N, Nolan SP (2009) Chem Rev 109:3612
Snead DR, Seo H, Hong S (2008) Curr Org Chem 12:1370
Lillo V, Prieto A, Bonet A, Díaz-Requejo MM, Ramírez J, Pérez PJ, Fernández E (2009) Organometallics 28:659
Fleming WJ, Müller-Bunz H, Lillo V, Fernández E, Guiry PJ (2009) Org Biomol Chem 7:2520
Hirsch-Weil D, Abboud KA, Hong S (2010) Chem Commun 46:7525
Park JK, Lackey HH, Rexford MD, Kovnir K, Shatruk M, McQuade DT (2010) Org Lett 12:5008
Zhao L, Ma Y, He F, Duan W, Chen J, Song C (2013) J Org Chem 78:1677
Iwai T, Akiyama Y, Sawamura M (2013) Tetrahedron Asymmetry 24:729
Krause N (ed) (2002) Modern organocopper chemistry. Wiley-VCH, Weinheim
O’Brien JM, Lee K, Hoveyda AH (2010) J Am Chem Soc 132:10630
Feng X, Yun J (2010) Chem Eur J 16:13609
Chen IH, Kanai M, Shibasaki M (2010) Org Lett 12:4098
Feng X, Yun J (2009) Chem Commun 6577
Chen IH, Yin L, Itano W, Kanai M, Shibasaki M (2009) J Am Chem Soc 131:11664
Solé C, Whiting A, Gulyás H, Fernández E (2011) Adv Synth Catal 353:376
Solé C, Bonet A, de Vries AHM, de Vries JG, Lefort L, Gulyás H, Fernández E (2012) Organometallics 31:7855
Calow ADJ, Batsanov AS, Pujol A, Solé C, Fernández E, Whiting A (2013) Org Lett 15:4810
Ibrahem I, Breistein P, Córdova A (2011) Angew Chem Int Ed 50:12036
He ZT, Zhao YS, Tian ZP, Wang CC, Dong HQ, Lin GQ (2014) Org Lett 16:1426
Kobayashi S, Xu P, Endo T, Ueno M, Kitanosono T (2012) Angew Chem Int Ed 51:12763
Luo Y, Roy ID, Madec AGE, Lam HW (2014) Angew Chem Int Ed 53:4186
Thorpe SB, Guo X, Santos WL (2011) Chem Commun 424
Yuan W, Zhang X, Yu Y, Ma S (2013) Chem Eur J 19:7193
Shiomi T, Adachi T, Toribatake K, Zhou L, Nishiyama H (2009) Chem Commun 5987
Hirano K, Yorimitsu H, Oshima K (2007) Org Lett 9:5031
Lillo V, Geier MJ, Westcott SA, Fernández E (2009) Org Biomol Chem 7:4674
Gao M, Thorpe SB, Santos WL (2009) Org Lett 11:3478
Lee K, Zhugralin AR, Hoveyda AH (2009) J Am Chem Soc 131:7253
Kleeberg C, Crawford AG, Batsanov AS, Hodgkinson P, Apperley DC, Cheung MS, Lin Z, Marder TB (2011) J Org Chem 77:785
Radomkit S, Hoveyda AH (2014) Angew Chem Int Ed 53:3387
Ibrahem I, Breistein P, Córdova A (2012) Chem Eur J 18:5175
Lindstroem UM (ed) (2007) Organic reactions in water. Wiley-Blackwell, Oxford
Chea H, Sim HS, Yun J (2010) Bull Korean Chem Soc 31:551
Thorpe SB, Calderone JA, Santos WL (2012) Org Lett 14:1918
Molander GA, McKee SA (2011) Org Lett 13:4684
Kitanosono T, Xu P, Kobayashi S (2014) Chem Asian J 9:179
Kitanosono T, Xu P, Kobayashi S (2013) Chem Commun 49:8184
Stavber G, Casar Z (2013) Appl Organomet Chem 27:159
Hansen KB, Balsells J, Dreher S, Hsiao Y, Kubryk M, Palucki M, Rivera N, Steinhuebel D, Armstrong JD III, Askin D, Grabowski EJJ (2005) Org Process Res Dev 9:634
Burns AR, González JS, Lam HW (2012) Angew Chem Int Ed 51:10827
Semba K, Nakao Y (2014) J Am Chem Soc 136:7567
Acknowledgments
We are grateful for the financial support of the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (2013R1A1A2058160).
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2015 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Lee, S., Yun, J. (2015). Asymmetric Catalytic Borylation of α,β-Unsaturated Acceptors. In: Fernández, E., Whiting, A. (eds) Synthesis and Application of Organoboron Compounds. Topics in Organometallic Chemistry, vol 49. Springer, Cham. https://doi.org/10.1007/978-3-319-13054-5_3
Download citation
DOI: https://doi.org/10.1007/978-3-319-13054-5_3
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-13053-8
Online ISBN: 978-3-319-13054-5
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)