Starks, C. M. Phase-transfer catalysis. I. Heterogeneous reactions involving anion transfer by quaternary ammonium and phosphonium salts. J. Am. Chem. Soc. 93, 195–199 (1971).

Article  CAS  Google Scholar 

Makosza, M. Two-phase reactions in the chemistry of carbanions and halocarbenes–a useful tool in organic synthesis. Pure Appl. Chem. 43, 439–462 (1975).

Article  CAS  Google Scholar 

Makosza, M. Reactions of organic anions. XI. Catalytic alkylation of indene. Tetrahedron Lett. 7, 4621–4624 (1966).

Article  Google Scholar 

Starks, C. M., Liotta, C. L. & Halpern, M. Phase-transfer Catalysis (Springer, 1994).

Weber, W. P. & Gokel, G. W. Phase Transfer Catalysis in Organic Synthesis, Vol. 4 (Springer, 1977).

Sasson, Y. & Neumann, R. (eds) Handbook of Phase Transfer Catalysis (Blackie Academic & Professional, 1997).

Makosza, M. Phase-transfer catalysis. A general green methodology in organic synthesis. Pure Appl. Chem. 72, 1399–1403 (2000).

Article  CAS  Google Scholar 

Shirakawa, S. & Maruoka, K. Recent developments in asymmetric phase-transfer reactions. Angew. Chem. Int. Ed. 52, 4312–4348 (2013).

Article  CAS  Google Scholar 

Hashimoto, T. & Maruoka, K. Recent development and application of chiral phase-transfer catalysts. Chem. Rev. 107, 5656–5682 (2007).

Article  CAS  PubMed  Google Scholar 

Albanese, D. & Penso, M. New trends in asymmetric phase transfer catalysis. Eur. J. Org. Chem. 26, e202300224 (2023).

Article  CAS  Google Scholar 

Lee, H. J. & Maruoka, K. Recent asymmetric phase-transfer catalysis with chiral binaphthyl-modified and related phase-transfer catalysts over the last 10 years. Chem. Rec. 23, e202200286 (2023).

Article  CAS  PubMed  Google Scholar 

Helder, R., Hummelen, J. C., Laane, R. W. P. M., Wiering, J. S. & Wynberg, H. Catalytic asymmetric induction in oxidation reactions. The synthesis of optically active epoxides. Tetrahedron Lett. 17, 1831–1834 (1976).

Article  Google Scholar 

Dolling, U. H., Davis, P. & Grabowski, E. J. Efficient catalytic asymmetric alkylations. 1. Enantioselective synthesis of (+)-indacrinone via chiral phase-transfer catalysis. J. Am. Chem. Soc. 106, 446–447 (1984).

Article  CAS  Google Scholar 

O’Donnell, M. J., Bennett, W. D. & Wu, S. The stereoselective synthesis of α-amino acids by phase-transfer catalysis. J. Am. Chem. Soc. 111, 2353–2355 (1989).

Article  Google Scholar 

Lygo, B. & Wainwright, P. G. A new class of asymmetric phase-transfer catalysts derived from Cinchona alkaloids–application in the enantioselective synthesis of α-amino acids. Tetrahedron Lett. 38, 8595–8598 (1997).

Article  CAS  Google Scholar 

Corey, E. J., Xu, F. & Noe, M. C. A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions. J. Am. Chem. Soc. 119, 12414–12415 (1997).

Article  CAS  Google Scholar 

Ooi, T., Kameda, M. & Maruoka, K. Molecular design of a C2-symmetric chiral phase-transfer catalyst for practical asymmetric synthesis of α-amino acids. J. Am. Chem. Soc. 121, 6519–6520 (1999).

Article  CAS  Google Scholar 

Otevrel, J & Waser, M. in Asymmetric Organocatalysis: New Strategies, Catalysts, and Opportunities (eds Albrecht, Ł. et al.) 71–120 (Wiley-VCH, 2023).

Shibuguchi, T. et al. Development of new asymmetric two-center catalysts in phase-transfer reactions. Tetrahedron Lett. 43, 9539–9543 (2002).

Article  CAS  Google Scholar 

Kitamura, M., Shirakawa, S. & Maruoka, K. Powerful chiral phase-transfer catalysts for the asymmetric synthesis of α-alkyl- and α, α-dialkyl-α-amino acids. Angew. Chem. Int. Ed. 44, 1549–1551 (2005).

Article  CAS  Google Scholar 

He, R., Wang, X., Hashimoto, T. & Maruoka, K. Binaphthyl-modified quaternary phosphonium salts as chiral phase-transfer catalysts: asymmetric amination of β‐keto esters. Angew. Chem. Int. Ed. 47, 9466–9468 (2008).

Article  CAS  Google Scholar 

Uraguchi, D., Asai, Y. & Ooi, T. Site-directed asymmetric quaternization of a peptide backbone at a C-terminal azlactone. Angew. Chem. Int. Ed. 48, 733–737 (2009).

Article  CAS  Google Scholar 

Denmark, S. E., Gould, N. D. & Wolf, L. M. A systematic investigation of quaternary ammonium ions as asymmetric phase-transfer catalysts. Synthesis of catalyst libraries and evaluation of catalyst activity. J. Org. Chem. 76, 4260–4336 (2011).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Ma, T. et al. Pentanidium-catalyzed enantioselective phase-transfer conjugate addition reactions. J. Am. Chem. Soc. 133, 2828–2831 (2011).

Article  CAS  PubMed  Google Scholar 

Wang, C., Zong, L. & Tan, C.-H. Enantioselective oxidation of alkenes with potassium permanganate catalyzed by chiral dicationic bisguanidinium. J. Am. Chem. Soc. 137, 10677–10682 (2015).

Article  CAS  PubMed  Google Scholar 

Rauniyar, V., Lackner, A. D., Hamilton, G. L. & Toste, F. D. Asymmetric electrophilic fluorination using an anionic chiral phase-transfer catalyst. Science 334, 1681–1684 (2011).

Article  CAS  PubMed  Google Scholar 

Pupo, G. et al. Asymmetric nucleophilic fluorination under hydrogen bonding phase-transfer catalysis. Science 360, 638–642 (2018).

Article  CAS  PubMed  Google Scholar 

Lygo, B. & Andrews, B. I. Asymmetric phase-transfer catalysis utilizing chiral quaternary ammonium salts: asymmetric alkylation of glycine imines. Acc. Chem. Res. 37, 518–525 (2004).

Article  CAS  PubMed  Google Scholar 

Cannizzaro, C. E. & Houk, K. Magnitudes and chemical consequences of R3N+–C–H…O=C hydrogen bonding. J. Am. Chem. Soc. 124, 7163–7169 (2002).

Article  CAS  PubMed  Google Scholar 

Reetz, M. T., Huette, S. & Goddard, R. Tetrabutylammonium salts of CH-acidic carbonyl compounds: real carbanions or supramolecules? J. Am. Chem. Soc. 115, 9339–9340 (1993).

Article  CAS  Google Scholar 

Maruoka, K. Design of high-performance chiral phase-transfer catalysts with privileged structures. Proc. Jpn Acad. Ser. B 95, 1–16 (2019).

Article  CAS  Google Scholar 

Jew, S.-s. & Park, H.-g. Cinchona-based phase-transfer catalysts for asymmetric synthesis. Chem. Commun. 7090–7103 (2009).

Arai, S. Tsuji, R. Nishida, A. Phase-transfer-catalyzed asymmetric Michael reaction using newly-prepared chiral quaternary ammonium salts derived from L-tartrate. Tetrahedron Lett. 43, 9535–9537 (2002).

Article  CAS  Google Scholar 

Park, H.-G. et al. Highly enantioselective and practical cinchona-derived phase-transfer catalysts for the synthesis of α-amino acids. Angew. Chem. Int. Ed. 41, 3036–3038 (2002).

Article  CAS  Google Scholar 

Kita, T., Georgieva, A., Hashimoto, Y., Nakata, T. & Nagasawa, K. C2-Symmetric chiral pentacyclic guanidine: a phase-transfer catalyst for the asymmetric alkylation of tert-butyl glycinate Schiff base. Angew. Chem. Int. Ed. 41, 2832–2834 (2002).

Article  CAS  Google Scholar 

Xu, C. et al. Development of C2-symmetric chiral spirocyclic phase-transfer catalysts: synthesis and application to asymmetric alkylation of glycinate Schiff base. Org. Lett. 23, 2890–2894 (2021).

Article  CAS  PubMed  Google Scholar 

Foster, D., Moggach, S. A. & Dorta, R. Accessing phase-transfer catalysts and a phosphoramidite ligand via the asymmetric intramolecular hydroamination reaction. Organometallics 42, 1513–1524 (2023).

Article  CAS  Google Scholar 

Oh, J., Park, J. & Nahm, K. Counter-rotatable dual cinchona quinuclidinium salts and their phase transfer catalysis in enantioselective alkylation of glycine imines. Chem. Commun. 57, 6816–6819 (2021).

Article  CAS  Google Scholar 

Li, S., Zhou, H. & List, B. Synthesis and resolution of an axially chiral spirocyclic quaternary ammonium ion-based phase-transfer catalyst. Asian J. Org. Chem. 12, e202300241 (2023).

Article  CAS  Google Scholar 

Majdecki, M., Niedbala, P. & Jurczak, J. Amide-based Cinchona alkaloids as phase-transfer catalysts: synthesis and potential application. Org. Lett. 21, 8085–8090 (2019).