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Chiral Phosphorus–Olefin Ligands for the RhI‐Catalyzed Asymmetric Addition of Aryl Boronic Acids to Electron‐Deficient Olefins
dc.contributor.authorChen, Qian
dc.contributor.authorLi, Liang
dc.contributor.authorZhou, Guangli
dc.contributor.authorMa, Xiaoli
dc.contributor.authorZhang, Lu
dc.contributor.authorGuo, Fang
dc.contributor.authorLuo, Yi
dc.contributor.authorXia, Wujiong
dc.date.accessioned2017-06-16T20:07:14Z
dc.date.available2017-06-16T20:07:14Z
dc.date.issued2016-05-20
dc.identifier.citationChen, Qian; Li, Liang; Zhou, Guangli; Ma, Xiaoli; Zhang, Lu; Guo, Fang; Luo, Yi; Xia, Wujiong (2016). "Chiral Phosphorus–Olefin Ligands for the RhI‐Catalyzed Asymmetric Addition of Aryl Boronic Acids to Electron‐Deficient Olefins." Chemistry – An Asian Journal 11(10): 1518-1522.
dc.identifier.issn1861-4728
dc.identifier.issn1861-471X
dc.identifier.urihttps://hdl.handle.net/2027.42/137195
dc.description.abstractNew chiral phosphorus–olefin hybrid ligands derived from the rigid “privileged” l‐proline have been conveniently prepared and applied in the rhodium‐catalyzed asymmetric arylation of electron‐deficient olefins with arylboronic acids at room temperature; this reaction provides the desired products in excellent yields and high enantioselectivities. The origin of observed stereoselectivity has been investigated by density functional theory (DFT) calculations.New chiral phosphorus–olefin hybrid ligands derived from l‐proline have been conveniently prepared and applied in the rhodium‐catalyzed asymmetric arylation of electron‐deficient olefins with arylboronic acids at room temperature. This reaction provides the desired products in excellent yields with high enantioselectivity. The origin of observed stereoselectivity has been investigated by density functional theory (DFT) calculations.
dc.publisherSpringer
dc.publisherWiley Periodicals, Inc.
dc.subject.otherelectron-deficient olefins
dc.subject.otherasymmetric arylation
dc.subject.otherL-proline
dc.subject.otherligands
dc.subject.otherrhodium
dc.titleChiral Phosphorus–Olefin Ligands for the RhI‐Catalyzed Asymmetric Addition of Aryl Boronic Acids to Electron‐Deficient Olefins
dc.typeArticleen_US
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137195/1/asia201600143.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137195/2/asia201600143-sup-0001-misc_information.pdf
dc.identifier.doi10.1002/asia.201600143
dc.identifier.sourceChemistry – An Asian Journal
dc.identifier.citedreferenceY. Li, M.-H. Xu, Chem. Commun. 2014, 50, 3771; For sulfoxide-olefins ligands, see:
dc.identifier.citedreferenceG. Chen, J. Gui, P. Cao, J. Liao, Tetrahedron 2012, 68, 3220;
dc.identifier.citedreferenceW.-Y. Qi, T.-S. Zhu, M.-H. Xu, Org. Lett. 2011, 13, 3410;
dc.identifier.citedreferenceT. Thaler, L.-N. Guo, A. K. Steib, M. Raducan, K. Karaghiosoff, P. Mayer, P. Knochel, Org. Lett. 2011, 13, 3182;
dc.identifier.citedreferenceF. Xue, D. Wang, X. Li, B. Wan, J. Org. Chem. 2012, 77, 3071.
dc.identifier.citedreferenceFor sulfonamide–olefins ligands, see:
dc.identifier.citedreferenceH. Wang, T. Jiang, M.-H. Xu, J. Am. Chem. Soc. 2013, 135, 971;
dc.identifier.citedreferenceT.-S. Zhu, S.-S. Jin, M.-H. Xu, Angew. Chem. Int. Ed. 2012, 51, 780; Angew. Chem. 2012, 124, 804;
dc.identifier.citedreferenceS.-S. Jin, H. Wang, M.-H. Xu, Chem. Commun. 2011, 47, 7230;
dc.identifier.citedreferenceX. Feng, Y. Nie, J. Yang, H. Du, Org. Lett. 2012, 14, 624;
dc.identifier.citedreferenceX. Feng, Y. Wang, B. Wei, J. Yang, H. Du, Org. Lett. 2011, 13, 3300;
dc.identifier.citedreferenceX. Feng, B. Wei, J. Yang, H. Du, Org. Biomol. Chem. 2011, 9, 5927;
dc.identifier.citedreferenceY. Wang, X. Feng, H. Du, Org. Lett. 2011, 13, 4954;
dc.identifier.citedreferenceD. W. Low, G. Pattison, M. D. Wieczysty, G. H. Churchill, H. W. Lam, Org. Lett. 2012, 14, 2548.
dc.identifier.citedreference 
dc.identifier.citedreferenceQ. Chen, C. Chen, F. Guo, W. Xia, Chem. Commun. 2013, 49, 6433;
dc.identifier.citedreferenceQ. Chen, L. Li, F. Guo, Z. Mao, Tetrahedron 2015, DOI: 10.1016/j.tet.2015.01.054.
dc.identifier.citedreferenceSee the Supporting Information for details. ( S )-(−)-1-Boc-2-pyrrolidinemethanol can be conveniently prepared from l -proline by protection and reduction on a gram scale. However, it can be bought at a price of 150 US $/100 g from Energy Chemical, Shanghai, China.
dc.identifier.citedreferenceJ. M. Hoover, S. S. Stahl, J. Am. Chem. Soc. 2011, 133, 16901.
dc.identifier.citedreference 
dc.identifier.citedreferenceK. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169;
dc.identifier.citedreferenceT. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829;
dc.identifier.citedreferenceH. J. Edwards, J. D. Hargrave, S. D. Penrose, C. G. Frost, Chem. Soc. Rev. 2010, 39, 2093;
dc.identifier.citedreferenceP. Tian, H.-Q. Dong, G.-Q. Lin, ACS Catal. 2012, 2, 95.
dc.identifier.citedreferenceA. G. Schultz, R. E. Harrington, J. Am. Chem. Soc. 1991, 113, 4926.
dc.identifier.citedreferenceF. M. Bickelhaupt, E. J. Baerends in Reviews in Computational Chemistry, Vol. 15 (Eds.: K. B. Lipkowitz, D. B. Boyd ), Wiley-VCH, New York, 2000, pp.  1 – 86.
dc.identifier.citedreference 
dc.identifier.citedreferenceComprehensive Asymmetric Catalysis I–III (Eds.: E. N.Jacobsen, A. Pfaltz, H. Yamamoto ), Springer, New York, 1999;
dc.identifier.citedreferenceCatalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima ), Wiley-VCH, New York, 2000.
dc.identifier.citedreference 
dc.identifier.citedreferencePrivileged Chiral Ligands and Catalysts (Ed.: Q.-L.Zhou ), Wiley-VCH, Weinheim, 2011;
dc.identifier.citedreferencePhosphorus Ligands in Asymmetric Catalysis 1–3 (Eds.: A. Börner ), Wiley-VCH, Weinheim, 2008.
dc.identifier.citedreferenceFor reviews, see:
dc.identifier.citedreferenceF. Glorius, Angew. Chem. Int. Ed. 2004, 43, 3364; Angew. Chem. 2004, 116, 3444;
dc.identifier.citedreferenceJ. B. Johnson, T. Rovis, Angew. Chem. Int. Ed. 2008, 47, 840; Angew. Chem. 2008, 120, 852;
dc.identifier.citedreferenceC. Defieber, H. Grützmacher, E. M. Carreira, Angew. Chem. Int. Ed. 2008, 47, 4482; Angew. Chem. 2008, 120, 4558;
dc.identifier.citedreferenceR. Shintani, T. Hayashi, Aldrichimica Acta 2009, 42, 31;
dc.identifier.citedreferenceC.-G. Feng, M.-H. Xu, G.-Q. Lin, Synlett 2011, 1345;
dc.identifier.citedreferenceX. Feng, H. Du, Asian J. Org. Chem. 2012, 1, 204.
dc.identifier.citedreference 
dc.identifier.citedreferenceT. Hayashi, K. Ueyama, N. Tokunaga, K. Yoshida, J. Am. Chem. Soc. 2003, 125, 11508;
dc.identifier.citedreferenceC. Fischer, C. Defieber, T. Suzuki, E. M. Carreira, J. Am. Chem. Soc. 2004, 126, 1628.
dc.identifier.citedreferenceFor selected examples of chiral diene ligands with bicyclic skeleton, see:
dc.identifier.citedreferenceN. Tokunaga, Y. Otomaru, K. Okamoto, K. Ueyama, R. Shintani, T. Hayashi, J. Am. Chem. Soc. 2004, 126, 13584;
dc.identifier.citedreferenceJ.-F. Paquin, C. Defieber, C. R. J. Stephenson, E. M. Carreira, J. Am. Chem. Soc. 2005, 127, 10850;
dc.identifier.citedreferenceK. Okamoto, T. Hayashi, V. H. Rawal, Org. Lett. 2008, 10, 4387;
dc.identifier.citedreferenceR. Shintani, K. Okamoto, T. Hayashi, Org. Lett. 2005, 7, 4757;
dc.identifier.citedreferenceR. Shintani, M. Takeda, Y.-T. Soh, T. Ito, T. Hayashi, Org. Lett. 2011, 13, 2977;
dc.identifier.citedreferenceC. Defieber, J.-F. Paquin, S. Serna, E. M. Carreira, Org. Lett. 2004, 6, 3873;
dc.identifier.citedreferenceK. Aikawa, S. Akutagawa, K. Mikami, J. Am. Chem. Soc. 2006, 128, 12648;
dc.identifier.citedreferenceZ.-Q. Wang, C.-G. Feng, M.-H. Xu, G.-Q. Lin, J. Am. Chem. Soc. 2007, 129, 5336;
dc.identifier.citedreferenceC.-G. Feng, Z.-Q. Wang, C. Shao, M.-H. Xu, G.-Q. Lin, Org. Lett. 2008, 10, 4101;
dc.identifier.citedreferenceZ. Cui, H.-J. Yu, R.-F. Yang, W.-Y. Gao, C.-G. Feng, G.-Q. Lin, J. Am. Chem. Soc. 2011, 133, 12394;
dc.identifier.citedreferenceH.-Y. Yang, M.-H. Xu, Chem. Commun. 2010, 46, 9223;
dc.identifier.citedreferenceS. Helbig, S. Sauer, N. Cramer, S. Laschat, A. Baro, W. Frey, Adv. Synth. Catal. 2007, 349, 2331;
dc.identifier.citedreferenceT. Gendrineau, O. Chuzel, H. Eijsberg, J.-P. Genet, S. Darses, Angew. Chem. Int. Ed. 2008, 47, 7669; Angew. Chem. 2008, 120, 7783;
dc.identifier.citedreferenceM. K. Brown, E. J. Corey, Org. Lett. 2010, 12, 172;
dc.identifier.citedreferenceY. Luo, A. J. Carnell, Angew. Chem. Int. Ed. 2010, 49, 2750; Angew. Chem. 2010, 122, 2810;
dc.identifier.citedreferenceG. Pattison, G. Piraux, H. W. Lam, J. Am. Chem. Soc. 2010, 132, 14373;
dc.identifier.citedreferenceT. Gendrineau, J.-P. Genet, S. Darses, Org.Lett. 2009, 11, 3486;
dc.identifier.citedreferenceY.-C. Chung, D. Janmanchi, H.-L. Wu, Org.Lett. 2012, 14, 2766.
dc.identifier.citedreferenceFor selected examples of chiral diene ligands with acyclic skeleton, see:
dc.identifier.citedreferenceX. Hu, M. Zhuang, Z. Cao, H. Du, Org. Lett. 2009, 11, 4744;
dc.identifier.citedreferenceZ. Cao, H. Du, Org. Lett. 2010, 12, 2602;
dc.identifier.citedreferenceX. Hu, Z. Cao, Z. Liu, Y. Wang, H. Du, Adv. Synth. Catal. 2010, 352, 651;
dc.identifier.citedreferenceY. Wang, X. Hu, H. Du, Org. Lett. 2010, 12, 5482;
dc.identifier.citedreferenceY. Liu, H. Du, J. Am. Chem. Soc. 2013, 135, 6810;
dc.identifier.citedreferenceB. M. Trost, A. C. Burns, T. Tautz, Org.Lett. 2011, 13, 4566;
dc.identifier.citedreferenceQ. Li, Z. Dong, Z.-X. Yu, Org. Lett. 2011, 13, 1122.
dc.identifier.citedreferenceFor selected examples of chiral phosphorus-olefin ligands, see:
dc.identifier.citedreferenceP. Maire, S. Deblon, F. Breher, J. Geier, C. Böhler, H. Rüegger, H. Schönberg, H. Grützmacher, Chem. Eur. J. 2004, 10, 4198;
dc.identifier.citedreferenceE. Piras, F. Läng, H. Rüegger, D. Stein, M. Wörle, H. Grützmacher, Chem. Eur. J. 2006, 12, 5849;
dc.identifier.citedreferenceR. Shintani, W.-L. Duan, T. Nagano, A. Okada, T. Hayashi, Angew. Chem. Int. Ed. 2005, 44, 4611; Angew. Chem. 2005, 117, 4687;
dc.identifier.citedreferenceP. Kasák, V. B. Arion, M. Widhalm, Tetrahedron: Asymmetry 2006, 17, 3084;
dc.identifier.citedreferenceR. T. Stemmler, C. Bolm, Synlett 2007, 1365;
dc.identifier.citedreferenceW.-L. Duan, H. Iwamura, R. Shintani, T. Hayashi, J. Am. Chem. Soc. 2007, 129, 2130;
dc.identifier.citedreferenceT. Minuth, M. M. K. Boysen, Org.Lett. 2009, 11, 4212;
dc.identifier.citedreferenceR. Shintani, R. Narui, Y. Tsutsumi, S. Hayashi, T. Hayashi, Chem. Commun. 2011, 47, 6123;
dc.identifier.citedreferenceT. Nishimura, Y. Maeda, T. Hayashi, Org. Lett. 2011, 13, 3674;
dc.identifier.citedreferenceE. Drinkel, A. Briceño, R. Dorta, R. Dorta, Organometallics 2010, 29, 2503;
dc.identifier.citedreferenceH. Grugel, F. Albrecht, T. Minuth, M. M. K. Boysen, Org. Lett. 2012, 14, 3780;
dc.identifier.citedreferenceC. Defieber, M. A. Ariger, P. Moriel, E. M. Carreira, Angew. Chem. Int. Ed. 2007, 46, 3139; Angew. Chem. 2007, 119, 3200;
dc.identifier.citedreferenceT. J. Hoffman, E. M. Carreira, Angew. Chem. Int. Ed. 2011, 50, 10670; Angew. Chem. 2011, 123, 10858.
dc.identifier.citedreference 
dc.identifier.citedreferenceB. T. Hahn, F. Tewes, R. Fröhlich, F. Glorius, Angew. Chem. Int. Ed. 2010, 49, 1143; Angew. Chem. 2010, 122, 1161;
dc.identifier.citedreferenceN. Schröder, T. Besset, F. Glorius, Adv. Synth. Catal. 2012, 354, 579;
dc.identifier.citedreferenceN. Kuuloja, J. Tois, R. Franzén, Tetrahedron: Asymmetry 2011, 22, 468.
dc.identifier.citedreferenceFor a review, see:
dc.identifier.citedreferenceG. Chen, J. Gui, L. Li, J. Liao, Angew. Chem. Int. Ed. 2011, 50, 7681; Angew. Chem. 2011, 123, 7823;
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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