Topics in Current Chemistry (2019) 377:31
1 3
3. O’Donnell MJ (2004) The enantioselective synthesis of α-amino acids by phase-transfer catalysis
with achiral Schiff base esters. Acc Chem Res 37:506–517
4. Lygo B, Andrew BI (2004) Asymmetric phase-transfer catalysis utilizing chiral quaternary ammonium salts: asymmetric alkylation of glycine imines. Acc Chem Res 37:518–525
5. Ooi T, Maruoka K (2007) Recent advances in asymmetric phase-transfer catalysis. Angew Chem Int
Ed 46:4222–4266
6. Hashimoto T, Maruoka K (2007) Recent development and application of chiral phase-transfer catalysts. Chem Rev 107:5656–5682
7. O’Donnell MJ, Bennett WD, Wu S (1989) The stereoselective synthesis of α-amino acids by phasetransfer catalysis. J Am Chem Soc 111:2353–2355
8. Lipkowitz KB, Cavanaugh MW, Baker B, O’Donnell MJ (1991) Theoretical studies in molecular
recognition: asymmetric induction of benzophenone imine ester enolates by the benzylcinchoninium ion. J Org Chem 56:5181–5192
9. Ooi T, Kameda M, Maruoka K (1999) Molecular design of a C 2 -symmetric chiral phase-transfer
catalyst for practical asymmetric synthesis of α-amino acids. J Am Chem Soc 121:6519–6520
10. Ooi T, Kameda M, Maruoka K (2003) Design of N-spiro C2-symmetric chiral quaternary ammonium bromides as novel chiral phase-transfer catalysts: synthesis and application to practical asymmetric synthesis of α-amino acids. J Am Chem Soc 125:5139–5151
11. Kitamura M, Shirakawa S, Maruoka K (2005) 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
12. Chen G, Deng Y, Gong L, Mi A, Cui X, Jiang Y, Choi MCK, Chan ASC (2001) Palladium-catalyzed allylic alkylation of tert-butyl (diphenylmethylene)-glycinate with simple allyl esters under
chiral phase transfer conditions. Tetrahedron Asymmetry 12:1567–1571
13. Nakoji M, Kanayama T, Okino T, Takemoto Y (2001) Chiral phosphine-free Pd-mediated asymmetric allylation of prochiral enolate with a chiral phase-transfer catalyst. Org Lett 3:3329–3331
14. Nakoji M, Kanayama T, Okino T, Takemoto Y (2002) Pd-catalyzed asymmetric allylic alkylation of
glycine imino ester using a chiral phase-transfer catalyst. J Org Chem 67:7418–7423
15. Wuts PGM, Ashford SA (2008) A new approach to the synthesis of the carbon framework of
SC-84536, an inducible nitric oxide synthase inhibitor. Tetrahedron Lett 49:4033–4035
16. Kanayama T, Yoshida K, Miyabe H, Kimachi T, Takemoto Y (2003) Synthesis of β-substituted
α-amino acids with use of iridium-catalyzed asymmetric allylic substitution. J Org Chem
68:6197–6201
17. Kanayama T, Yoshida K, Miyabe H, Takemoto Y (2003) Enantio- and diastereoselective Ir-catalyzed allylic substitutions for asymmetric synthesis of amino acid derivatives. Angew Chem Int Ed
42:2054–2056
18. Su YL, Li YH, Chen YG, Han ZY (2017) Ir/PTC cooperatively catalyzed asymmetric umpolung
allylation of α-imino ester enabled synthesis of α-quaternary amino acid derivatives bearing two
vicinal stereocenters. Chem Commun 53:1985–1988
19. Wu Y, Hu L, Deng L (2015) Catalytic asymmetric umpolung reactions of imines. Nature
523:445–450
20. Ooi T, Uematsu Y, Maruoka K (2006) Asymmetric Strecker reaction of aldimines using aqueous
potassium cyanide by phase-transfer catalysis of chiral quaternary ammonium salts with a tetranaphthyl backbone. J Am Chem Soc 128:2548–2549
21. Ooi T, Ohara D, Tamura M, Maruoka K (2004) Design of new chiral phase-transfer catalysts with
dual functions for highly enantioselective epoxidation of α, β-unsaturated ketones. J Am Chem Soc
126:6844–6845
22. Uyanik M, Okamoto H, Yasui T, Ishihara K (2010) Quaternary ammonium (hypo)iodite catalysis
for enantioselective oxidative cycloetherification. Science 328:1376–1379
23. Bhunnoo RA, Hu Y, Lainé DI, Brown RCD (2002) An asymmetric phase-transfer dihydroxylation
reaction. Angew Chem Int Ed 41:3479–3480
24. Wang C, Zong L, Tan CH (2015) Enantioselective oxidation of alkenes with potassium permanganate catalyzed by chiral dicationic bisguanidinium. J Am Chem Soc 137:10677–10682
25. Ye X, Moeljadi AMP, Chin KF, Hirao H, Zong L, Tan CH (2016) Enantioselective sulfoxidation catalyzed by a bisguanidinium diphosphatobisperoxotungstate ion pair. Angew Chem Int Ed
55:7101–7105
26. Sato K, Aoki M, Ogawa M, Hashimoto T, Noyori R (1996) A practical method for epoxidation of terminal olefins with 30% hydrogen peroxide under halide-free conditions. J Org Chem
61:8310–8311
Reprinted from the journal
150
1 3
3. O’Donnell MJ (2004) The enantioselective synthesis of α-amino acids by phase-transfer catalysis
with achiral Schiff base esters. Acc Chem Res 37:506–517
4. Lygo B, Andrew BI (2004) Asymmetric phase-transfer catalysis utilizing chiral quaternary ammonium salts: asymmetric alkylation of glycine imines. Acc Chem Res 37:518–525
5. Ooi T, Maruoka K (2007) Recent advances in asymmetric phase-transfer catalysis. Angew Chem Int
Ed 46:4222–4266
6. Hashimoto T, Maruoka K (2007) Recent development and application of chiral phase-transfer catalysts. Chem Rev 107:5656–5682
7. O’Donnell MJ, Bennett WD, Wu S (1989) The stereoselective synthesis of α-amino acids by phasetransfer catalysis. J Am Chem Soc 111:2353–2355
8. Lipkowitz KB, Cavanaugh MW, Baker B, O’Donnell MJ (1991) Theoretical studies in molecular
recognition: asymmetric induction of benzophenone imine ester enolates by the benzylcinchoninium ion. J Org Chem 56:5181–5192
9. Ooi T, Kameda M, Maruoka K (1999) Molecular design of a C 2 -symmetric chiral phase-transfer
catalyst for practical asymmetric synthesis of α-amino acids. J Am Chem Soc 121:6519–6520
10. Ooi T, Kameda M, Maruoka K (2003) Design of N-spiro C2-symmetric chiral quaternary ammonium bromides as novel chiral phase-transfer catalysts: synthesis and application to practical asymmetric synthesis of α-amino acids. J Am Chem Soc 125:5139–5151
11. Kitamura M, Shirakawa S, Maruoka K (2005) 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
12. Chen G, Deng Y, Gong L, Mi A, Cui X, Jiang Y, Choi MCK, Chan ASC (2001) Palladium-catalyzed allylic alkylation of tert-butyl (diphenylmethylene)-glycinate with simple allyl esters under
chiral phase transfer conditions. Tetrahedron Asymmetry 12:1567–1571
13. Nakoji M, Kanayama T, Okino T, Takemoto Y (2001) Chiral phosphine-free Pd-mediated asymmetric allylation of prochiral enolate with a chiral phase-transfer catalyst. Org Lett 3:3329–3331
14. Nakoji M, Kanayama T, Okino T, Takemoto Y (2002) Pd-catalyzed asymmetric allylic alkylation of
glycine imino ester using a chiral phase-transfer catalyst. J Org Chem 67:7418–7423
15. Wuts PGM, Ashford SA (2008) A new approach to the synthesis of the carbon framework of
SC-84536, an inducible nitric oxide synthase inhibitor. Tetrahedron Lett 49:4033–4035
16. Kanayama T, Yoshida K, Miyabe H, Kimachi T, Takemoto Y (2003) Synthesis of β-substituted
α-amino acids with use of iridium-catalyzed asymmetric allylic substitution. J Org Chem
68:6197–6201
17. Kanayama T, Yoshida K, Miyabe H, Takemoto Y (2003) Enantio- and diastereoselective Ir-catalyzed allylic substitutions for asymmetric synthesis of amino acid derivatives. Angew Chem Int Ed
42:2054–2056
18. Su YL, Li YH, Chen YG, Han ZY (2017) Ir/PTC cooperatively catalyzed asymmetric umpolung
allylation of α-imino ester enabled synthesis of α-quaternary amino acid derivatives bearing two
vicinal stereocenters. Chem Commun 53:1985–1988
19. Wu Y, Hu L, Deng L (2015) Catalytic asymmetric umpolung reactions of imines. Nature
523:445–450
20. Ooi T, Uematsu Y, Maruoka K (2006) Asymmetric Strecker reaction of aldimines using aqueous
potassium cyanide by phase-transfer catalysis of chiral quaternary ammonium salts with a tetranaphthyl backbone. J Am Chem Soc 128:2548–2549
21. Ooi T, Ohara D, Tamura M, Maruoka K (2004) Design of new chiral phase-transfer catalysts with
dual functions for highly enantioselective epoxidation of α, β-unsaturated ketones. J Am Chem Soc
126:6844–6845
22. Uyanik M, Okamoto H, Yasui T, Ishihara K (2010) Quaternary ammonium (hypo)iodite catalysis
for enantioselective oxidative cycloetherification. Science 328:1376–1379
23. Bhunnoo RA, Hu Y, Lainé DI, Brown RCD (2002) An asymmetric phase-transfer dihydroxylation
reaction. Angew Chem Int Ed 41:3479–3480
24. Wang C, Zong L, Tan CH (2015) Enantioselective oxidation of alkenes with potassium permanganate catalyzed by chiral dicationic bisguanidinium. J Am Chem Soc 137:10677–10682
25. Ye X, Moeljadi AMP, Chin KF, Hirao H, Zong L, Tan CH (2016) Enantioselective sulfoxidation catalyzed by a bisguanidinium diphosphatobisperoxotungstate ion pair. Angew Chem Int Ed
55:7101–7105
26. Sato K, Aoki M, Ogawa M, Hashimoto T, Noyori R (1996) A practical method for epoxidation of terminal olefins with 30% hydrogen peroxide under halide-free conditions. J Org Chem
61:8310–8311
Reprinted from the journal
150