Topics in Current Chemistry (2020) 378:9
1 3
26. Sorimachi K, Terada M (2008) Relay catalysis by a metal-complex/Bronsted acid binary system in
a tandem isomerization/carbon-carbon bond forming sequence. J Am Chem Soc 130(44):14452–
14453. https ://doi.org/10.1021/ja807 591m
27. Cai Q, Liang XW, Wang SG, You SL (2013) An olefin isomerization/asymmetric Pictet-Spengler
cascade via sequential catalysis of ruthenium alkylidene and chiral phosphoric acid. Org Biomol
Chem 11(10):1602–1605. https ://doi.org/10.1039/c3ob0 0072a
28. Hansen CL, Clausen JW, Ohm RG, Ascic E, Le Quement ST, Tanner D, Nielsen TE (2013) Ruthenium hydride/Bronsted acid-catalyzed tandem isomerization/N-acyliminium cyclization sequence
for the synthesis of tetrahydro-beta-carbolines. J Org Chem 78(24):12545–12565. https ://doi.
org/10.1021/jo402 192s
29. Toda Y, Terada M (2013) Relay catalysis by a ruthenium complex-chiral bronsted acid binary sytem
for ternary reaction sequence involving enantioselective pictet-spengler-type cyclization as the key
step. Synlett 24(6):752–756. https ://doi.org/10.1055/s-0032-13183 02
30. Bernardez R, Suarez J, Fananas-Mastral M, Varela JA, Saá C (2016) Tandem long distance chainwalking/cyclization via RuH 2 (CO)(PPh 3 ) 3 /Bronsted acid catalysis: entry to aromatic oxazaheterocycles. Org Lett 18(4):642–645. https ://doi.org/10.1021/acs.orgle tt.5b034 99
31. Terada M, Toda Y (2009) Double bond isomerization/enantioselective aza-Petasis-Ferrier rearrangement sequence as an efficient entry to anti- and enantioenriched beta-amino aldehydes. J Am
Chem Soc 131(18):6354–6355. https ://doi.org/10.1021/ja902 202g
32. Richmond E, Khan IU, Moran J (2016) Enantioselective and regiodivergent functionalization of
n-allylcarbamates by mechanistically divergent multicatalysis. Chem Eur J 22(35):12274–12277.
https ://doi.org/10.1002/chem.20160 2792
33. Miura T, Nishida Y, Morimoto M, Murakami M (2013) Enantioselective synthesis of anti homoallylic alcohols from terminal alkynes and aldehydes based on concomitant use of a cationic iridium complex and a chiral phosphoric acid. J Am Chem Soc 135(31):11497–11500. https ://doi.
org/10.1021/ja405 790t
34. Miura T, Nakahashi J, Murakami M (2017) Enantioselective synthesis of (e)-delta-boryl-substituted anti-homoallylic alcohols using palladium and a chiral phosphoric acid. Angew Chem Int Ed
56(24):6989–6993. https ://doi.org/10.1002/anie.20170 2611
35. Miura T, Nakahashi J, Zhou W, Shiratori Y, Stewart SG, Murakami M (2017) Enantioselective
synthesis of anti-1,2-Oxaborinan-3-enes from aldehydes and 1,1-di(boryl)alk-3-enes using ruthenium and chiral phosphoric acid catalysts. J Am Chem Soc 139(31):10903–10908. https ://doi.
org/10.1021/jacs.7b064 08
36. Schuster M, Blechert S (1997) Olefin metathesis in organic chemistry. Angew Chem Int Ed
36(19):2037–2056. https ://doi.org/10.1002/anie.19972 0361
37. Furstner A (2000) Olefin metathesis and beyond a list of abbreviations can be found at the end of
this article. Angew Chem Int Ed 39(17):3012–3043
38. Grubbs RH (2004) Olefin metathesis. Tetrahedron 60(34):7117–7140. https ://doi.org/10.1016/j.
tet.2004.05.124
39. Vougioukalakis GC, Grubbs RH (2010) Ruthenium-based heterocyclic carbene-coordinated olefin
metathesis catalysts. Chem Rev 110(3):1746–1787. https ://doi.org/10.1021/cr900 2424
40. Cai Q, Zhao ZA, You SL (2009) Asymmetric construction of polycyclic indoles through olefin
cross-metathesis/intramolecular Friedel-Crafts alkylation under sequential catalysis. Angew Chem
Int Ed 48(40):7428–7431. https ://doi.org/10.1002/anie.20090 3462
41. Cai Q, Liang XW, Wang SG, Zhang JW, Zhang X, You SL (2012) Ring-closing metathesis/isomerization/Pictet-Spengler cascade via ruthenium/chiral phosphoric acid sequential catalysis. Org Lett
14(19):5022–5025. https ://doi.org/10.1021/ol302 215u
42. You S-L, Zhou Y, Liu X-W, Gu Q (2015) Enantioselective synthesis of tetrahydroindolizines
via ruthenium-chiral phosphoric acid sequential catalysis. Synlett 27(04):586–590. https ://doi.
org/10.1055/s-0035-15604 85
43. Zhang JW, Liu XW, Gu Q, Shi XX, You SL (2015) Enantioselective synthesis of 4,5,6,7-tetrahydroindoles via olefin cross-metathesis/intramolecular Friedel-Crafts alkylation reaction of pyrroles.
Org Chem Front 2(5):476–480. https ://doi.org/10.1039/c5qo0 0034c
44. Ascic E, Jensen JF, Nielsen TE (2011) Synthesis of heterocycles through a ruthenium-catalyzed
tandem ring-closing metathesis/isomerization/N-acyliminium cyclization sequence. Angew Chem
Int Ed 50(22):5188–5191. https ://doi.org/10.1002/anie.20110 0417
Reprinted from the journal
202
1 3
26. Sorimachi K, Terada M (2008) Relay catalysis by a metal-complex/Bronsted acid binary system in
a tandem isomerization/carbon-carbon bond forming sequence. J Am Chem Soc 130(44):14452–
14453. https ://doi.org/10.1021/ja807 591m
27. Cai Q, Liang XW, Wang SG, You SL (2013) An olefin isomerization/asymmetric Pictet-Spengler
cascade via sequential catalysis of ruthenium alkylidene and chiral phosphoric acid. Org Biomol
Chem 11(10):1602–1605. https ://doi.org/10.1039/c3ob0 0072a
28. Hansen CL, Clausen JW, Ohm RG, Ascic E, Le Quement ST, Tanner D, Nielsen TE (2013) Ruthenium hydride/Bronsted acid-catalyzed tandem isomerization/N-acyliminium cyclization sequence
for the synthesis of tetrahydro-beta-carbolines. J Org Chem 78(24):12545–12565. https ://doi.
org/10.1021/jo402 192s
29. Toda Y, Terada M (2013) Relay catalysis by a ruthenium complex-chiral bronsted acid binary sytem
for ternary reaction sequence involving enantioselective pictet-spengler-type cyclization as the key
step. Synlett 24(6):752–756. https ://doi.org/10.1055/s-0032-13183 02
30. Bernardez R, Suarez J, Fananas-Mastral M, Varela JA, Saá C (2016) Tandem long distance chainwalking/cyclization via RuH 2 (CO)(PPh 3 ) 3 /Bronsted acid catalysis: entry to aromatic oxazaheterocycles. Org Lett 18(4):642–645. https ://doi.org/10.1021/acs.orgle tt.5b034 99
31. Terada M, Toda Y (2009) Double bond isomerization/enantioselective aza-Petasis-Ferrier rearrangement sequence as an efficient entry to anti- and enantioenriched beta-amino aldehydes. J Am
Chem Soc 131(18):6354–6355. https ://doi.org/10.1021/ja902 202g
32. Richmond E, Khan IU, Moran J (2016) Enantioselective and regiodivergent functionalization of
n-allylcarbamates by mechanistically divergent multicatalysis. Chem Eur J 22(35):12274–12277.
https ://doi.org/10.1002/chem.20160 2792
33. Miura T, Nishida Y, Morimoto M, Murakami M (2013) Enantioselective synthesis of anti homoallylic alcohols from terminal alkynes and aldehydes based on concomitant use of a cationic iridium complex and a chiral phosphoric acid. J Am Chem Soc 135(31):11497–11500. https ://doi.
org/10.1021/ja405 790t
34. Miura T, Nakahashi J, Murakami M (2017) Enantioselective synthesis of (e)-delta-boryl-substituted anti-homoallylic alcohols using palladium and a chiral phosphoric acid. Angew Chem Int Ed
56(24):6989–6993. https ://doi.org/10.1002/anie.20170 2611
35. Miura T, Nakahashi J, Zhou W, Shiratori Y, Stewart SG, Murakami M (2017) Enantioselective
synthesis of anti-1,2-Oxaborinan-3-enes from aldehydes and 1,1-di(boryl)alk-3-enes using ruthenium and chiral phosphoric acid catalysts. J Am Chem Soc 139(31):10903–10908. https ://doi.
org/10.1021/jacs.7b064 08
36. Schuster M, Blechert S (1997) Olefin metathesis in organic chemistry. Angew Chem Int Ed
36(19):2037–2056. https ://doi.org/10.1002/anie.19972 0361
37. Furstner A (2000) Olefin metathesis and beyond a list of abbreviations can be found at the end of
this article. Angew Chem Int Ed 39(17):3012–3043
38. Grubbs RH (2004) Olefin metathesis. Tetrahedron 60(34):7117–7140. https ://doi.org/10.1016/j.
tet.2004.05.124
39. Vougioukalakis GC, Grubbs RH (2010) Ruthenium-based heterocyclic carbene-coordinated olefin
metathesis catalysts. Chem Rev 110(3):1746–1787. https ://doi.org/10.1021/cr900 2424
40. Cai Q, Zhao ZA, You SL (2009) Asymmetric construction of polycyclic indoles through olefin
cross-metathesis/intramolecular Friedel-Crafts alkylation under sequential catalysis. Angew Chem
Int Ed 48(40):7428–7431. https ://doi.org/10.1002/anie.20090 3462
41. Cai Q, Liang XW, Wang SG, Zhang JW, Zhang X, You SL (2012) Ring-closing metathesis/isomerization/Pictet-Spengler cascade via ruthenium/chiral phosphoric acid sequential catalysis. Org Lett
14(19):5022–5025. https ://doi.org/10.1021/ol302 215u
42. You S-L, Zhou Y, Liu X-W, Gu Q (2015) Enantioselective synthesis of tetrahydroindolizines
via ruthenium-chiral phosphoric acid sequential catalysis. Synlett 27(04):586–590. https ://doi.
org/10.1055/s-0035-15604 85
43. Zhang JW, Liu XW, Gu Q, Shi XX, You SL (2015) Enantioselective synthesis of 4,5,6,7-tetrahydroindoles via olefin cross-metathesis/intramolecular Friedel-Crafts alkylation reaction of pyrroles.
Org Chem Front 2(5):476–480. https ://doi.org/10.1039/c5qo0 0034c
44. Ascic E, Jensen JF, Nielsen TE (2011) Synthesis of heterocycles through a ruthenium-catalyzed
tandem ring-closing metathesis/isomerization/N-acyliminium cyclization sequence. Angew Chem
Int Ed 50(22):5188–5191. https ://doi.org/10.1002/anie.20110 0417
Reprinted from the journal
202