1 3
Topics in Current Chemistry (2020) 378:9
5. Doyle AG, Jacobsen EN (2007) Small-molecule H-bond donors in asymmetric catalysis. Chem
Rev 107(12):5713–5743. https ://doi.org/10.1021/cr068 373r
6. Mukherjee S, Yang JW, Hoffmann S, List B (2007) Asymmetric enamine catalysis. Chem Rev
107(12):5471–5569. https ://doi.org/10.1021/cr068 4016
7. Lee JM, Na Y, Han H, Chang S (2004) Cooperative multi-catalyst systems for one-pot organic
transformations. Chem Soc Rev 33(5):302–312. https ://doi.org/10.1039/b3090 33g
8. Allen AE, Macmillan DW (2012) Synergistic catalysis: a powerful synthetic strategy for new
reaction development. Chem Sci 3:633–658. https ://doi.org/10.1039/C2SC0 0907B
9. 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 12(11):1567–1571. https ://doi.org/10.1016/s0957
-4166(01)00276 -2
10. 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(21):3329–
3331. https ://doi.org/10.1021/ol016 567h
11. Park YJ, Park J-W, Jun C-H (2008) Metal-organic cooperative catalysis in C-H and C-C bond
activation and its concurrent recovery. ACC Chem Res 41(2):222–234. https ://doi.org/10.1021/
ar700 133y
12. Shao Z, Zhang H (2009) Combining transition metal catalysis and organocatalysis: a broad new
concept for catalysis. Chem Soc Rev 38(9):2745–2755. https ://doi.org/10.1039/b9012 58n
13. Du Z, Shao Z (2013) Combining transition metal catalysis and organocatalysis an update. Chem
Soc Rev 42(3):1337–1378. https ://doi.org/10.1039/c2cs3 5258c
14. Chen DF, Han ZY, Zhou XL, Gong LZ (2014) Asymmetric organocatalysis combined with metal
catalysis: concept, proof of concept, and beyond. Acc Chem Res 47(8):2365–2377. https ://doi.
org/10.1021/ar500 101a
15. Wu X, Li ML, Gong LZ (2013) Asymmetric relay catalysis reaction consisting of metal complex
and chiral phosphoric acids. Acta Chim Sinica 71(8):1091–1100. https ://doi.org/10.6023/A1303
0279
16. Yang ZP, Zhang W, You SL (2014) Catalytic asymmetric reactions by metal and chiral phosphoric acid sequential catalysis. J Org Chem 79(17):7785–7798. https ://doi.org/10.1021/jo501
300k
17. Uraguchi D, Terada M (2004) Chiral Bronsted acid-catalyzed direct Mannich reactions via electrophilic activation. J Am Chem Soc 126(17):5356–5357. https ://doi.org/10.1021/ja049 1533
18. Akiyama T, Itoh J, Yokota K, Fuchibe K (2004) Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid. Angew Chem Int Ed 43(12):1566–1568. https ://doi.org/10.1002/
anie.20035 3240
19. Terada M (2010) Chiral phosphoric acids as versatile catalysts for enantioselective transformations.
Synthesis 12:1929–1982. https ://doi.org/10.1055/s-0029-12188 01
20. Yu J, Shi F, Gong LZ (2011) Bronsted-acid-catalyzed asymmetric multicomponent reactions for the
facile synthesis of highly enantioenriched structurally diverse nitrogenous heterocycles. ACC Chem
Res 44(11):1156–1171. https ://doi.org/10.1021/ar200 0343
21. Parmar D, Sugiono E, Raja S, Rueping M (2014) Complete field guide to asymmetric BINOL-phosphate derived Bronsted acid and metal catalysis: history and classification by mode of activation;
Bronsted acidity, hydrogen bonding, ion pairing, and metal phosphates. Chem Rev 114(18):9047–
9153. https ://doi.org/10.1021/cr500 1496
22. Wu H, He YP, Shi F (2015) Recent advances in chiral phosphoric acid catalyzed asymmetric reactions for the synthesis of enantiopure indole derivatives. Synthesis 47(14):1990–2016. https ://doi.
org/10.1055/s-0034-13788 37
23. Han ZY, Gong LZ (2018) Asymmetric organo/palladium combined catalysis. Prog Chem
30(5):505–512. https ://doi.org/10.7536/Pc171 206
24. Inamdar SM, Konala A, Patil NT (2014) When gold meets chiral Bronsted acid catalysts: extending
the boundaries of enantioselective gold catalysis. Chem Commun 50(96):15124–15135. https ://doi.
org/10.1039/c4cc0 4633a
25. Escoubet S, Gastaldi S, Bertrand M (2005) Methods for the cleavage of allylic and propargylic C–N
bonds in amines and amides-selected alternative applications of the 1,3-hydrogen shift. Eur J Org
Chem 18:3855–3873. https ://doi.org/10.1002/ejoc.20050 0204
Reprinted from the journal
201
Topics in Current Chemistry (2020) 378:9
5. Doyle AG, Jacobsen EN (2007) Small-molecule H-bond donors in asymmetric catalysis. Chem
Rev 107(12):5713–5743. https ://doi.org/10.1021/cr068 373r
6. Mukherjee S, Yang JW, Hoffmann S, List B (2007) Asymmetric enamine catalysis. Chem Rev
107(12):5471–5569. https ://doi.org/10.1021/cr068 4016
7. Lee JM, Na Y, Han H, Chang S (2004) Cooperative multi-catalyst systems for one-pot organic
transformations. Chem Soc Rev 33(5):302–312. https ://doi.org/10.1039/b3090 33g
8. Allen AE, Macmillan DW (2012) Synergistic catalysis: a powerful synthetic strategy for new
reaction development. Chem Sci 3:633–658. https ://doi.org/10.1039/C2SC0 0907B
9. 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 12(11):1567–1571. https ://doi.org/10.1016/s0957
-4166(01)00276 -2
10. 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(21):3329–
3331. https ://doi.org/10.1021/ol016 567h
11. Park YJ, Park J-W, Jun C-H (2008) Metal-organic cooperative catalysis in C-H and C-C bond
activation and its concurrent recovery. ACC Chem Res 41(2):222–234. https ://doi.org/10.1021/
ar700 133y
12. Shao Z, Zhang H (2009) Combining transition metal catalysis and organocatalysis: a broad new
concept for catalysis. Chem Soc Rev 38(9):2745–2755. https ://doi.org/10.1039/b9012 58n
13. Du Z, Shao Z (2013) Combining transition metal catalysis and organocatalysis an update. Chem
Soc Rev 42(3):1337–1378. https ://doi.org/10.1039/c2cs3 5258c
14. Chen DF, Han ZY, Zhou XL, Gong LZ (2014) Asymmetric organocatalysis combined with metal
catalysis: concept, proof of concept, and beyond. Acc Chem Res 47(8):2365–2377. https ://doi.
org/10.1021/ar500 101a
15. Wu X, Li ML, Gong LZ (2013) Asymmetric relay catalysis reaction consisting of metal complex
and chiral phosphoric acids. Acta Chim Sinica 71(8):1091–1100. https ://doi.org/10.6023/A1303
0279
16. Yang ZP, Zhang W, You SL (2014) Catalytic asymmetric reactions by metal and chiral phosphoric acid sequential catalysis. J Org Chem 79(17):7785–7798. https ://doi.org/10.1021/jo501
300k
17. Uraguchi D, Terada M (2004) Chiral Bronsted acid-catalyzed direct Mannich reactions via electrophilic activation. J Am Chem Soc 126(17):5356–5357. https ://doi.org/10.1021/ja049 1533
18. Akiyama T, Itoh J, Yokota K, Fuchibe K (2004) Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid. Angew Chem Int Ed 43(12):1566–1568. https ://doi.org/10.1002/
anie.20035 3240
19. Terada M (2010) Chiral phosphoric acids as versatile catalysts for enantioselective transformations.
Synthesis 12:1929–1982. https ://doi.org/10.1055/s-0029-12188 01
20. Yu J, Shi F, Gong LZ (2011) Bronsted-acid-catalyzed asymmetric multicomponent reactions for the
facile synthesis of highly enantioenriched structurally diverse nitrogenous heterocycles. ACC Chem
Res 44(11):1156–1171. https ://doi.org/10.1021/ar200 0343
21. Parmar D, Sugiono E, Raja S, Rueping M (2014) Complete field guide to asymmetric BINOL-phosphate derived Bronsted acid and metal catalysis: history and classification by mode of activation;
Bronsted acidity, hydrogen bonding, ion pairing, and metal phosphates. Chem Rev 114(18):9047–
9153. https ://doi.org/10.1021/cr500 1496
22. Wu H, He YP, Shi F (2015) Recent advances in chiral phosphoric acid catalyzed asymmetric reactions for the synthesis of enantiopure indole derivatives. Synthesis 47(14):1990–2016. https ://doi.
org/10.1055/s-0034-13788 37
23. Han ZY, Gong LZ (2018) Asymmetric organo/palladium combined catalysis. Prog Chem
30(5):505–512. https ://doi.org/10.7536/Pc171 206
24. Inamdar SM, Konala A, Patil NT (2014) When gold meets chiral Bronsted acid catalysts: extending
the boundaries of enantioselective gold catalysis. Chem Commun 50(96):15124–15135. https ://doi.
org/10.1039/c4cc0 4633a
25. Escoubet S, Gastaldi S, Bertrand M (2005) Methods for the cleavage of allylic and propargylic C–N
bonds in amines and amides-selected alternative applications of the 1,3-hydrogen shift. Eur J Org
Chem 18:3855–3873. https ://doi.org/10.1002/ejoc.20050 0204
Reprinted from the journal
201