1 3
Topics in Current Chemistry (2020) 378:9
45. Shi YC, Wang SG, Yin Q, You SL (2014) N-alkylation of indole via ring-closing metathesis/
isomerization/Mannich cascade under ruthenium/chiral phosphoric acid sequential catalysis. Org
Chem Front 1(1):39–43. https ://doi.org/10.1039/c3qo0 0008g
46. Inamdar SM, Chakrabarty I, Patil NT (2016) A unified approach to pyrrole-embedded aza-heterocyclic scaffolds based on the RCM/isomerization/cyclization cascade catalyzed by a Ru/B-H binary
catalyst system. RSC Adv 6(41):34428–34433. https ://doi.org/10.1039/c6ra0 5646f
47. Han ZY, Xiao H, Chen XH, Gong LZ (2009) Consecutive intramolecular hydroamination/asymmetric transfer hydrogenation under relay catalysis of an achiral gold complex/chiral Bronsted acid
binary system. J Am Chem Soc 131(26):9182–9183. https ://doi.org/10.1021/ja903 547q
48. Liu XY, Che CM (2009) Highly enantioselective synthesis of chiral secondary amines by gold(I)/
chiral Bronsted acid catalyzed tandem intermolecular hydroamination and transfer hydrogenation
reactions. Org Lett 11(18):4204–4207. https ://doi.org/10.1021/ol901 443b
49. Shinde VS, Mane MV, Vanka K, Mallick A, Patil NT (2015) Gold(I)/chiral Bronsted acid catalyzed enantioselective hydroamination-hydroarylation of alkynes: the effect of a remote hydroxyl
group on the reactivity and enantioselectivity. Chem Eur J 21(3):975–979. https ://doi.org/10.1002/
chem.20140 5061
50. Zhao F, Li N, Zhu YF, Han ZY (2016) Enantioselective construction of functionalized tetrahydrocarbazoles enabled by asymmetric relay catalysis of gold complex and chiral Bronsted acid. Org
Lett 18(7):1506–1509. https ://doi.org/10.1021/acs.orgle tt.6b000 12
51. Han ZY, Guo R, Wang PS, Chen DF, Xiao H, Gong LZ (2011) Enantioselective concomitant creation of vicinal quaternary stereogenic centers via cyclization of alkynols triggered addition of azlactones. Tetrahedron Lett 52(45):5963–5967. https ://doi.org/10.1016/j.tetle t.2011.08.123
52. Cala L, Mendoza A, Fananas FJ, Rodriguez F (2013) A catalytic multicomponent coupling reaction for the enantioselective synthesis of spiroacetals. Chem Commun 49(26):2715–2717. https ://
doi.org/10.1039/c3cc0 0118k
53. Wu H, He YP, Gong LZ (2013) Direct access to enantioenriched spiroacetals through asymmetric relay catalytic three-component reaction. Org Lett 15(3):460–463. https ://doi.org/10.1021/ol303
188u
54. Han ZY, Chen DF, Wang YY, Guo R, Wang PS, Wang C, Gong LZ (2012) Hybrid metal/organo
relay catalysis enables enynes to be latent dienes for asymmetric Diels-Alder reaction. J Am Chem
Soc 134(15):6532–6535. https ://doi.org/10.1021/ja300 7148
55. Wang PS, Li KN, Zhou XL, Wu X, Han ZY, Guo R, Gong LZ (2013) Enantioselective relay
catalytic cascade intramolecular hydrosiloxylation and Mukaiyama aldol reaction. Chem Eur J
19(20):6234–6238. https ://doi.org/10.1002/chem.20130 0702
56. Gong L-Z, Li N, Chen D-F, Wang P-S, Han Z-Y (2014) Relay catalytic cascade hydrosiloxylation and asymmetric Hetero-Diels–Alder reaction. Synthesis 46(10):1355–1361. https ://doi.
org/10.1055/s-0033-13409 05
57. Wu X, Li ML, Wang PS (2014) Hybrid gold/chiral Bronsted acid relay catalysis allows an enantioselective synthesis of (-)-5-epi-eupomatilone-6. J Org Chem 79(1):419–425. https ://doi.org/10.1021/
jo402 4232
58. Rexit AA, Mailikezati M (2015) Asymmetric synthesis of optically active spiroacetals from alkynyl glycols catalyzed by gold complex/Bronsted acid binary system. Tetrahedron Lett 56(21):2651–
2655. https ://doi.org/10.1016/j.tetle t.2015.03.007
59. Inamdar SM, Gonnade RG, Patil NT (2017) Synthesis of annulated bis-indoles through Au(i)/Bronsted acid-catalyzed reactions of (1H-indol-3-yl)(aryl)methanols with 2-(arylethynyl)-1H-indoles.
Org Biomol Chem 15(4):863–869. https ://doi.org/10.1039/c6ob0 2595a
60. Qian D, Zhang J (2013) Gold/Bronsted acid relay catalysis for enantioselective construction of spirocyclic diketones. Chem Eur J 19(22):6984–6988. https ://doi.org/10.1002/chem.20130 1208
61. Liu RR, Ye SC, Lu CJ, Zhuang GL, Gao JR, Jia YX (2015) Dual catalysis for the redox annulation
of nitroalkynes with indoles: enantioselective construction of indolin-3-ones bearing quaternary stereocenters. Angew Chem Int Ed 54(38):11205–11208. https ://doi.org/10.1002/anie.20150 4697
62. Villa-Marcos B, Xiao JL (2015) Metal and organo-catalysed asymmetric hydroaminomethylation of
styrenes. Chin J Catal 36(1):106–112. https ://doi.org/10.1016/S1872 -2067(14)60246 -1
63. Meng J, Li XH, Han ZY (2017) Enantioselective hydroaminomethylation of olefins enabled by Rh/
Bronsted acid relay catalysis. Org Lett 19(5):1076–1079. https ://doi.org/10.1021/acs.orgle tt.7b001 00
64. Meng J, Fan L-F, Han Z-Y, Gong L-Z (2018) α-quaternary chiral aldehydes from styrenes,
allylic alcohols, and syngas via multi-catalyst relay catalysis. Chem 4(5):1047–1058. https ://doi.
org/10.1016/j.chemp r.2018.03.010
Reprinted from the journal
203
Topics in Current Chemistry (2020) 378:9
45. Shi YC, Wang SG, Yin Q, You SL (2014) N-alkylation of indole via ring-closing metathesis/
isomerization/Mannich cascade under ruthenium/chiral phosphoric acid sequential catalysis. Org
Chem Front 1(1):39–43. https ://doi.org/10.1039/c3qo0 0008g
46. Inamdar SM, Chakrabarty I, Patil NT (2016) A unified approach to pyrrole-embedded aza-heterocyclic scaffolds based on the RCM/isomerization/cyclization cascade catalyzed by a Ru/B-H binary
catalyst system. RSC Adv 6(41):34428–34433. https ://doi.org/10.1039/c6ra0 5646f
47. Han ZY, Xiao H, Chen XH, Gong LZ (2009) Consecutive intramolecular hydroamination/asymmetric transfer hydrogenation under relay catalysis of an achiral gold complex/chiral Bronsted acid
binary system. J Am Chem Soc 131(26):9182–9183. https ://doi.org/10.1021/ja903 547q
48. Liu XY, Che CM (2009) Highly enantioselective synthesis of chiral secondary amines by gold(I)/
chiral Bronsted acid catalyzed tandem intermolecular hydroamination and transfer hydrogenation
reactions. Org Lett 11(18):4204–4207. https ://doi.org/10.1021/ol901 443b
49. Shinde VS, Mane MV, Vanka K, Mallick A, Patil NT (2015) Gold(I)/chiral Bronsted acid catalyzed enantioselective hydroamination-hydroarylation of alkynes: the effect of a remote hydroxyl
group on the reactivity and enantioselectivity. Chem Eur J 21(3):975–979. https ://doi.org/10.1002/
chem.20140 5061
50. Zhao F, Li N, Zhu YF, Han ZY (2016) Enantioselective construction of functionalized tetrahydrocarbazoles enabled by asymmetric relay catalysis of gold complex and chiral Bronsted acid. Org
Lett 18(7):1506–1509. https ://doi.org/10.1021/acs.orgle tt.6b000 12
51. Han ZY, Guo R, Wang PS, Chen DF, Xiao H, Gong LZ (2011) Enantioselective concomitant creation of vicinal quaternary stereogenic centers via cyclization of alkynols triggered addition of azlactones. Tetrahedron Lett 52(45):5963–5967. https ://doi.org/10.1016/j.tetle t.2011.08.123
52. Cala L, Mendoza A, Fananas FJ, Rodriguez F (2013) A catalytic multicomponent coupling reaction for the enantioselective synthesis of spiroacetals. Chem Commun 49(26):2715–2717. https ://
doi.org/10.1039/c3cc0 0118k
53. Wu H, He YP, Gong LZ (2013) Direct access to enantioenriched spiroacetals through asymmetric relay catalytic three-component reaction. Org Lett 15(3):460–463. https ://doi.org/10.1021/ol303
188u
54. Han ZY, Chen DF, Wang YY, Guo R, Wang PS, Wang C, Gong LZ (2012) Hybrid metal/organo
relay catalysis enables enynes to be latent dienes for asymmetric Diels-Alder reaction. J Am Chem
Soc 134(15):6532–6535. https ://doi.org/10.1021/ja300 7148
55. Wang PS, Li KN, Zhou XL, Wu X, Han ZY, Guo R, Gong LZ (2013) Enantioselective relay
catalytic cascade intramolecular hydrosiloxylation and Mukaiyama aldol reaction. Chem Eur J
19(20):6234–6238. https ://doi.org/10.1002/chem.20130 0702
56. Gong L-Z, Li N, Chen D-F, Wang P-S, Han Z-Y (2014) Relay catalytic cascade hydrosiloxylation and asymmetric Hetero-Diels–Alder reaction. Synthesis 46(10):1355–1361. https ://doi.
org/10.1055/s-0033-13409 05
57. Wu X, Li ML, Wang PS (2014) Hybrid gold/chiral Bronsted acid relay catalysis allows an enantioselective synthesis of (-)-5-epi-eupomatilone-6. J Org Chem 79(1):419–425. https ://doi.org/10.1021/
jo402 4232
58. Rexit AA, Mailikezati M (2015) Asymmetric synthesis of optically active spiroacetals from alkynyl glycols catalyzed by gold complex/Bronsted acid binary system. Tetrahedron Lett 56(21):2651–
2655. https ://doi.org/10.1016/j.tetle t.2015.03.007
59. Inamdar SM, Gonnade RG, Patil NT (2017) Synthesis of annulated bis-indoles through Au(i)/Bronsted acid-catalyzed reactions of (1H-indol-3-yl)(aryl)methanols with 2-(arylethynyl)-1H-indoles.
Org Biomol Chem 15(4):863–869. https ://doi.org/10.1039/c6ob0 2595a
60. Qian D, Zhang J (2013) Gold/Bronsted acid relay catalysis for enantioselective construction of spirocyclic diketones. Chem Eur J 19(22):6984–6988. https ://doi.org/10.1002/chem.20130 1208
61. Liu RR, Ye SC, Lu CJ, Zhuang GL, Gao JR, Jia YX (2015) Dual catalysis for the redox annulation
of nitroalkynes with indoles: enantioselective construction of indolin-3-ones bearing quaternary stereocenters. Angew Chem Int Ed 54(38):11205–11208. https ://doi.org/10.1002/anie.20150 4697
62. Villa-Marcos B, Xiao JL (2015) Metal and organo-catalysed asymmetric hydroaminomethylation of
styrenes. Chin J Catal 36(1):106–112. https ://doi.org/10.1016/S1872 -2067(14)60246 -1
63. Meng J, Li XH, Han ZY (2017) Enantioselective hydroaminomethylation of olefins enabled by Rh/
Bronsted acid relay catalysis. Org Lett 19(5):1076–1079. https ://doi.org/10.1021/acs.orgle tt.7b001 00
64. Meng J, Fan L-F, Han Z-Y, Gong L-Z (2018) α-quaternary chiral aldehydes from styrenes,
allylic alcohols, and syngas via multi-catalyst relay catalysis. Chem 4(5):1047–1058. https ://doi.
org/10.1016/j.chemp r.2018.03.010
Reprinted from the journal
203