Asymmetric Phase‐Transfer Catalysis – From Classical Applications to New Concepts

Chapter 3 Asymmetric Phase-Transfer Catalysis – From Classical Applications to New Concepts Jan Otevrel, Jan Otevrel Department of Chemical Drugs, Masaryk University, Brno, Czech RepublicSearch for more papers by this authorMario Waser, Mario Waser Institute of Organic Chemistry, Johannes Kepler University Linz, Austria, Linz, AustriaSearch for more papers by this author Jan Otevrel, Jan Otevrel Department of Chemical Drugs, Masaryk University, Brno, Czech RepublicSearch for more papers by this authorMario Waser, Mario Waser Institute of Organic Chemistry, Johannes Kepler University Linz, Austria, Linz, AustriaSearch for more papers by this author Book Editor(s):Łukasz Albrecht, Łukasz Albrecht Lodz University of Technology, Institute of Organic Chemistry, Żeromskiego 116, 90-924 Lodz, PolandSearch for more papers by this authorAnna Albrecht, Anna Albrecht Lodz University of Technology, Institute of General and Ecological Chemistry, Żeromskiego 116, 90-924 Lodz, PolandSearch for more papers by this authorLuca Dell'Amico, Luca Dell'Amico University of Padova, Department of Chemical Sciences, Via Marzolo 1, 53131 Padova, ItalySearch for more papers by this author First published: 18 November 2022 https://doi.org/10.1002/9783527832217.ch3 AboutPDFPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Summary Asymmetric (ion-pairing) phase-transfer catalysis has emerged as a powerful concept within the realm of asymmetric (organo)-catalysis over the course of the last four decades. Whereas early approaches mainly focused around the use of chiral ammonium salt catalysts for the control of enolate-type nucleophiles, the last years have witnessed a remarkable diversity of novel catalyst motives and new applications, reaching beyond what was classically considered as phase-transfer catalysis. As a consequence, a strict mechanistic classification of whether a reaction is really a phase-transfer-catalyzed process or not is also often not so easily possible anymore, underscoring the diversity of this field. Within this chapter, we wish to highlight the unique potential of chiral cationic, anionic, and neutral phase-transfer catalysts (PTCs) to facilitate challenging target transformations by discussing some of the, in our opinion, most important catalyst classes and applications thereof, with a special focus on some of the most recently introduced concepts. References For seminal reports in the field of phase-transfer catalysis see (a) Makosza , M. ( 1966 ). Tetrahedron Lett. 7 : 4621 – 4624 . (b) Makosza , M. ( 1966 ). Tetrahedron Lett. 7 : 5489 – 5492 . (c) Makosza , M. ( 1969 ). Tetrahedron Lett. 10 : 673 – 676 . (d) Makosza , M. ( 1969 ). Tetrahedron Lett. 10 : 677 – 678 . (e) Starks , C.M. ( 1971 ). J. Am. Chem. Soc. 93 : 195 – 199 . (f) Brändström , A. ( 1977 ). Adv. Phys. Org. Chem. 15 : 267 – 329 . (a) Dehmlow , E.W. and Dehmlow , S.S. ( 1993 ). Phase transfer catalysis , 3rd . Weinheim : VCH . (b) Starks , C.M. , Liotta , C.L. , and Halpern , M. ( 1994 ). Phase-Transfer Catalysis . New York : Chapman & Hall . (c) Sasson , Y. and Neumann , R. ( 1997 ). Handbook of Phase-Transfer Catalysis . London : Blackie Academic & Professional . For seminal reports in the field of asymmetric phase-transfer catalysis see (a) Helder , R. , Hummelen , J.C. , Laane , R.W.P.M. et al. ( 1976 ). Tetrahedron Lett. 17 : 1831 – 1834 . (b) Colonna , S. , Hiemstra , H. , and Wynberg , H. ( 1978 ). J. Chem. Soc., Chem. Commun. 238 – 239 . (c) Dolling , U.H. , Davis , P. , and Grabowski , E.J.J. ( 1984 ). J. Am. Chem. Soc. 106 : 446 – 447 . (d) O'Donnell , M.J. , Bennett , W.D. , and Wu , S. ( 1989 ). J. Am. Chem. Soc. 111 : 2353 – 2355 . (e) O'Donnell , M.J. , Wu , S. , and Huffman , J.C. ( 1994 ). Tetrahedron 50 : 4507 – 4518 . For general reviews about asymmetric ion pairing (phase-transfer) catalysis see (a) O'Donnell , M.J. ( 2000 ). Asymmetric phase-transfer reactions . In: Catalytic Asymmetric Syntheses , 2 e (ed. I. Ojima ), 727 – 755 . New York : Wiley-VCH . (b) Maruoka , K. ( 2008 ). Asymmetric Phase Transfer Catalysis . Weinheim : Wiley-VCH . (c) Shirakawa , S. and Maruoka , K. ( 2013 ). Angew. Chem. Int. Ed. 52 : 4312 – 4348 . (d) Brak , K. and Jacobsen , E.N. ( 2013 ). Angew. Chem. Int. Ed. 52 : 534 – 561 . For selected reviews discussing mainly chiral cation-based PTCs see (a) O'Donnell , M.J. ( 2004 ). Acc. Chem. Res. 37 : 506 – 517 . (b) Lygo , B. and Andrews , B.I. ( 2004 ). Acc. Chem. Res. 37 : 518 – 525 . (c) Hashimoto , T. and Maruoka , K. ( 2007 ). Chem. Rev. 107 : 5656 – 5682 . (d) Ooi , T. and Maruoka , K. ( 2007 ). Angew. Chem. Int. Ed. 46 : 4222 – 4266 . (e) Jew , S.-S. and Park , H.-G. ( 2009 ). Chem. Commun. 7090 – 7103 . (f) Tan , J. and Yasuda , N. ( 2015 ). Org. Process Res. Dev. 19 : 1731 – 1746 . (g) Kaneko , S. , Kumatabara , Y. , and Shirakawa , S. ( 2016 ). Org. Biomol. Chem. 14 : 5367 – 5376 . (h) Vitale , M.R. , Oudeyer , S. , Levacher , V. , and Brière , J.F. ( 2017 ) Radical and Ion-Pairing Strategies in Asymmetric Organocatalysis , Elsevier. (i) Qia, D., Sun, J. (2019). Chem. Eur. J. 25 : 3740 – 3751 . For selected overviews about chiral anion-based ion pairing catalysts: (a) Lacour , J. and Moraleda , D. ( 2009 ). Chem. Commun. 7073 – 7089 . (b) Phipps , R.J. , Hamilton , G.L. , and Toste , F.D. ( 2012 ). Nature Chem. 4 : 603 – 614 . (a) Zong , L. and Tan , C.-H. ( 2017 ). Acc. Chem. Res. 50 : 842 – 856 . (b) Patel , N. , Sood , R. , and Bharatam , P.V. ( 2018 ). Chem. Rev. 118 : 8770 – 8785 . (a) Maruoka , K. and Ooi , T. ( 2003 ). Chem. Rev. 103 : 3013 – 3028 . (b) O'Donnell , M.J. ( 2019 ). Tetrahedron 75 : 3667 – 3696 . For a review about asymmetric counteranion directed catalysis: Mahlau , M. and List , B. ( 2013 ). Angew. Chem. Int. Ed. 52 : 518 – 533 . For an overview about cooperative ion pairing catalysis: Waser , M. , Novacek , J. , and Gratzer , K. ( 2015 ). Cooperative catalysis involving chiral ion pair catalysts . In: Cooperative Catalysis (ed. R. Peters ), 197 – 226 . Weinheim : Wiley-VCH . For a recent review about chiral cation-directed transition metal catalysis: Ye , X. and Tan , C.-H. ( 2021 ). Chem. Sci. 12 : 533 – 539 . For a pioneering and a more recent example for the use of chiral metal-salen complexes as PTCs: (a) Belokon , Y.N. , North , M. , Kublitski , V.S. et al. ( 1999 ). Tetrahedron Lett. 40 : 6105 – 6108 . (b) Park , D. , Jette , C.I. , Kim , J. et al. ( 2020 ). Angew. Chem. Int. Ed. 59 : 775 – 779 . For two pioneering examples of chiral metal-based Lewis acids containing additional cationic ion pairing motives: (a) Kull , T. and Peters , R. ( 2008 ). Angew. Chem. Int. Ed. 47 : 5461 – 5464 . (b) Kull , T. , Cabrera , J. , and Peters , R. ( 2010 ). Chem. Eur. J. 16 : 9132 – 9139 . Lygo , B. and Wainwright , P.G. ( 1997 ). Tetrahedron Lett. 38 : 8595 – 8598 . Corey , E.J. , Xu , F. , and Noe , M.C. ( 1997 ). J. Am. Chem. Soc. 119 : 12414 – 12415 . Ha , M.W. and Park , H.-G. ( 2016 ). Cinchona alkaloid derivatives as asymmetric phase-transfer catalysts . In: Sustainable Catalysis: Without Metals or Other Endangered Elements, Part 2 (ed. M. North ), 82 – 134 . RSC Green Chemistry . Xiang , B. , Belyk , K.M. , Reamer , R.A. , and Yasuda , N. ( 2014 ). Angew. Chem. Int. Ed. 53 : 8375 – 8378 . Wang , Y. , Gao , Q. , Liu , Z. et al. ( 2018 ). J. Org. Chem. 83 : 2263 – 2273 . For pioneering examples: (a) Jew , S.-S. , Jeong , B.-S. , Yoo , M.-S. et al. ( 2001 ). Chem. Commun. 1244 – 1245 . (b) Chinchilla , R. , Mazón , P. , and Najera , C. ( 2002 ). Tetrahedron: Asymmetry 13 : 927 – 931 . (c) Siva , A. and Murugan , E. ( 2005 ). J. Mol. Catal. A.: Chem. 241 : 111 – 117 . (d) Wang , X. , Yin , L. , Yang , T. , and Wang , Y. ( 2007 ). Tetrahedron: Asymmetry 18 : 108 – 114 . For reviews about bifunctional ammonium salt catalysts see (a) Novacek , J. and Waser , M. ( 2013 ). Eur. J. Org. Chem. 637 – 648 . (b) Wang , H. ( 2019 ). Catalysts 9 : 244 . Wang , H. , Zheng , C. , and Zhao , G. ( 2019 ). Chin. J. Chem. 37 : 1111 – 1119 . (a) Bernal , P. , Fernandez , R. , and Lassaletta , J.M. ( 2010 ). Chem. Eur. J. 16 : 7714 – 7718 . (b) Schörgenhumer , J. , Otte , S. , Haider , V. et al. ( 2020 ). Tetrahedron 76 : 130816 . (a) Johnson , K.M. , Rattley , M.S. , Sladojevich , F. et al. ( 2012 ). Org. Lett. 14 : 2492 – 2495 . (b) Li , M. , Woods , P.A. , and Smith , M.D. ( 2013 ). Chem. Sci. 4 : 2907 – 2911 . (c) Wang , B. , Liu , Y. , Sun , C. et al. ( 2014 ). J. Org. Chem. 16 : 6432 – 6435 . (d) Wang , B. , Xu , T. , Zhu , L. et al. ( 2017 ). Org. Chem. Front. 4 : 1266 – 1271 . (e) Craig , R. , Litvajova , M. , Cronin , S.A. , and Connon , S.J. ( 2018 ). Chem. Commun. 54 : 10108 – 10111 . (f) Craig , R. , Sorrention , E. , and Connon , S.J. ( 2018 ). Chem. Eur. J. 24 : 4528 – 4531 . (g) Dinh , A.N. , Noorbehest , R.R. , Toenjes , S.T. et al. ( 2018 ). Synlett 29 : 2155 – 2160 . For analogous squaramides: Wang , B. , Hem , Y. , Fu , X. et al. ( 2015 ). Synlett 26 : 2588 – 2592 . (a) Majdecki , M. , Niedbala , P. , and Jurczak , J. ( 2019 ). Org. Lett. 21 : 8085 – 8090 . (b) Majdecki , M. , Tyszka-Gumkowska , A. , and Jurczak , J. ( 2020 ). Org. Lett. 22 : 8687 – 8691 . (c) Majdecki , M. , Grodek , P. , and Jurczak , J. ( 2021 ). J. Org. Chem. 86 : 995 – 1001 . Pioneering reports (a) Ooi , T. , Kameda , M. , and Maruoka , K.