View Item 

Show simple item record

Thiophosphoramide‐Based Cooperative Catalysts for Brønsted Acid Promoted Ionic Diels–Alder Reactions
dc.contributor.authorBorovika, Alinaen_US
dc.contributor.authorTang, Pui‐inen_US
dc.contributor.authorKlapman, Sethen_US
dc.contributor.authorNagorny, Pavelen_US
dc.date.accessioned2014-01-08T20:35:09Z
dc.date.available2015-02-03T16:14:40Zen_US
dc.date.issued2013-12-09en_US
dc.identifier.citationBorovika, Alina; Tang, Pui‐in ; Klapman, Seth; Nagorny, Pavel (2013). "Thiophosphoramideâ Based Cooperative Catalysts for Brønsted Acid Promoted Ionic Dielsâ Alder Reactions ." Angewandte Chemie International Edition 52(50): 13424-13428.en_US
dc.identifier.issn1433-7851en_US
dc.identifier.issn1521-3773en_US
dc.identifier.urihttps://hdl.handle.net/2027.42/102243
dc.publisherWILEY‐VCH Verlagen_US
dc.subject.otherHydrogen Bondsen_US
dc.subject.otherCooperative Catalysisen_US
dc.subject.otherCycloadditionen_US
dc.subject.otherOrganocatalysisen_US
dc.subject.otherSynthetic Methodsen_US
dc.titleThiophosphoramide‐Based Cooperative Catalysts for Brønsted Acid Promoted Ionic Diels–Alder Reactionsen_US
dc.typeArticleen_US
dc.rights.robotsIndexNoFollowen_US
dc.subject.hlbsecondlevelChemistryen_US
dc.subject.hlbtoplevelScienceen_US
dc.description.peerreviewedPeer Revieweden_US
dc.contributor.affiliationumDepartment of Chemistry, University of Michigan, Ann Arbor, MI 48109 (USA)en_US
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/102243/1/anie_201307133_sm_miscellaneous_information.pdf
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/102243/2/13424_ftp.pdf
dc.identifier.doi10.1002/anie.201307133en_US
dc.identifier.sourceAngewandte Chemie International Editionen_US
dc.identifier.citedreferenceThiophosphoramides as a one‐ and two‐hydrogen‐bond donors:en_US
dc.identifier.citedreferenceJ. H. Lee, W. H. Kim, S. J. Danishefsky, Tetrahedron Lett. 2010, 51, 1252.en_US
dc.identifier.citedreferenceThiourea‐based HBDs have been previously used in combination with sulfonic acids to promote Povarov reactions:en_US
dc.identifier.citedreferenceH. Xu, S. J. Zuend, M. G. Woll, Y. Tao, E. N. Jacobsen, Science 2010, 327, 986; For the selected examples of thiourea‐catalyzed DA reactions refer to:en_US
dc.identifier.citedreferenceA. Wittkopp, P. R. Schreiner, Chem. Eur. J. 2003, 9, 407;en_US
dc.identifier.citedreferenceM. P. Lalonde, M. A. McGowan, N. S. Rajapaksa, E. N. Jacobsen, J. Am. Chem. Soc. 2013, 135, 1891;en_US
dc.identifier.citedreferenceX. Jiang, L. Liu, P. Zhang, Y. Zhong, R. Wang, Angew. Chem. 2013, 125, 11539 – 11543; Angew. Chem. Int. Ed. 2013, 52, 11329 – 11333.en_US
dc.identifier.citedreference en_US
dc.identifier.citedreferenceJ. P. Malerich, K. Hagihara, V. H. Rawal, J. Am. Chem. Soc. 2008, 130, 14416;en_US
dc.identifier.citedreferenceN. Busschaert, I. L. Kirby, S. Young, S. J. Coles, P. N. Horton, M. E. Light, P. A. Gale, Angew. Chem. 2012, 124, 4502; Angew. Chem. Int. Ed. 2012, 51, 4426.en_US
dc.identifier.citedreferenceA. Lu, R. Wu, Y. Wang, Z. Zhou, G. Wu, J. Fang, C. Tang, Eur. J. Org. Chem. 2011, 122;en_US
dc.identifier.citedreferenceR. Wu, X. Chang, A. Lu, Y. Wang, G. Wu, H. Song, Z. Zhou, C. Tang, Chem. Commun. 2011, 47, 5034.en_US
dc.identifier.citedreferenceA. A. Rodriguez, H. Yoo, J. W. Ziller, K. J. Shea, Tetrahedron Lett. 2009, 50, 6830.en_US
dc.identifier.citedreferenceDuring the preparation of this manuscript, a study describing the anion recognition and transport properties of 7 e was published:en_US
dc.identifier.citedreferenceP. B. Cranwell, J. R. Hiscock, C. J. E. Haynes, M. E. Light, N. J. Wells, P. A. Gale, Chem. Commun. 2013, 49, 874. For a related study describing anion binding properties of three‐hydrogen‐bond donor catalysts refer to:en_US
dc.identifier.citedreferenceE. V. Beletskiy, J. Schmidt, X.‐B. Wang, S. R. Kass, J. Am. Chem. Soc. 2012, 134, 18534.en_US
dc.identifier.citedreferenceL. Pescatori, A. Arduini, A. Pochini, A. Secchi, C. Massera, F. Ugozzoli, Org. Biomol. Chem. 2009, 7, 3698.en_US
dc.identifier.citedreferenceE. J. Olson, P. Buhlmann, J. Org. Chem. 2011, 76, 8406.en_US
dc.identifier.citedreferenceWe thank Dr. Hynes for providing us permission to use WinEQNMR for calculating the K a of 7 e: M. J. Hynes, J. Chem. Soc. Dalton Trans. 1993, 311.en_US
dc.identifier.citedreference en_US
dc.identifier.citedreferenceF. Kniep, S. H. Jungbauer, Q. Zhang, S. M. Walter, S. Schindler, I. Schnapperelle, E. Herdtweck, S. M. Huber, Angew. Chem. 2013, 125, 7166; Angew. Chem. Int. Ed. 2013, 52, 7028;en_US
dc.identifier.citedreferenceS. Beckendorf, S. Asmus, C. Muck‐Lichtenfeld, O. G. Mancheño, Chem. Eur. J. 2013, 19, 1581.en_US
dc.identifier.citedreferenceSelected reviews:en_US
dc.identifier.citedreferenceA. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713;en_US
dc.identifier.citedreferenceZ. Zhang, P. R. Schreiner, Chem. Soc. Rev. 2009, 38, 1187;en_US
dc.identifier.citedreferenceK. Brak, E. N. Jacobsen, Angew. Chem. 2013, 125, 558; Angew. Chem. Int. Ed. 2013, 52, 534;en_US
dc.identifier.citedreferenceS. Beckendorf, S. Asmus, O. G. Mancheno, ChemCatChem 2012, 4, 926.en_US
dc.identifier.citedreferenceM. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901.en_US
dc.identifier.citedreference en_US
dc.identifier.citedreferenceS. E. Reisman, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 7198;en_US
dc.identifier.citedreferenceN. Z. Burns, M. R. Witten, E. N. Jacobsen, J. Am. Chem. Soc. 2011, 133, 14578;en_US
dc.identifier.citedreferenceA. R. Brown, W.‐H. Kuo, E. N. Jacobsen, J. Am. Chem. Soc. 2010, 132, 9286.en_US
dc.identifier.citedreferenceA. Borovika, P. Nagorny, Tetrahedron 2013, 69, 5719.en_US
dc.identifier.citedreference en_US
dc.identifier.citedreferenceT. Sasaki, Y. Ishibashi, M. Ohno, Tetrahedron Lett. 1982, 23, 1693;en_US
dc.identifier.citedreferenceW. R. Roush, H. R. Gillis, A. P. Essenfeld, J. Org. Chem. 1984, 49, 4674;en_US
dc.identifier.citedreferenceP. G. Gassman, D. A. Singleton, J. J. Wilwerding, S. P. Chavan, J. Am. Chem. Soc. 1987, 109, 2182;en_US
dc.identifier.citedreferenceP. G. Gassman, S. P. Chavan, Tetrahedron Lett. 1988, 29, 3407.en_US
dc.identifier.citedreference en_US
dc.identifier.citedreferenceM. Harmata, P. Rashatasakhon, Tetrahedron 2003, 59, 2371;en_US
dc.identifier.citedreferenceX. Jiang, R. Wang, Chem. Rev. 2013, 113, 5515.en_US
dc.identifier.citedreference en_US
dc.identifier.citedreferenceP. A. Grieco, J. L. Collins, S. T. Handy, Synlett 1995, 1155;en_US
dc.identifier.citedreferenceP. A. Grieco, M. D. Kaufman, J. F. Daeuble, N. Saito, J. Am. Chem. Soc. 1996, 118, 2095;en_US
dc.identifier.citedreferenceP. A. Grieco, J. J. Nunes, M. D. Gaul, J. Am. Chem. Soc. 1990, 112, 4595;en_US
dc.identifier.citedreferenceP. A. Grieco, Aldrichimica Acta 1991, 24, 59.en_US
dc.owningcollnameInterdisciplinary and Peer-Reviewed


Files in this item

Name:
anie_201307133_sm_miscellaneou ...
Size:
1.685MB
Format:
PDF
View/Open
Name:
13424_ftp.pdf
Size:
820.8KB
Format:
PDF
View/Open

Show simple item record

Remediation of Harmful Language

The University of Michigan Library aims to describe library materials in a way that respects the people and communities who create, use, and are represented in our collections. Report harmful or offensive language in catalog records, finding aids, or elsewhere in our collections anonymously through our metadata feedback form. More information at Remediation of Harmful Language.

Accessibility

If you are unable to use this file in its current format, please select the Contact Us link and we can modify it to make it more accessible to you.