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235. Kong D, Li M, Zi G, Hou G, He Y (2016) J Org Chem 81:6640
236. Hu XH, Hu XP (2019) Adv Synth Catal 361:5063
237. Mazuela J, Antonsson T, Knerr L, Marsden SP, Munday RH, Johansson MJ (2019) Adv Synth
Catal 361:578
238. Wang WB, Lu SM, Yang PY, Han XW, Zhou YG (2003) J Am Chem Soc 125:10536
239. Yang PY, Zhou YG (2004) Tetrahedron Asymmetry 15:1145
240. Wang DW, Wang XB, Wang DS, Lu SM, Zhou YG, Li YX (2009) J Org Chem 74:2780.
Later, it was shown that an electronically deficient ligand synthesized from (S)-MeO-BiPhep
showed an increase of the activity and enantioselectivity: Zhang DY, Wang DS, Wang MC,
Yu CB, Gao K, Zhou YG (2011) Synthesis 2796
241. Lu SM, Wang YQ, Han XW, Zhou YG (2006) Angew Chem Int Ed 45:2260
242. Shi L, Ye ZS, Cao LL, Guo RN, Hu Y, Zhou YG (2012) Angew Chem Int Ed 51:8286
243. Hu SB, Zhai XY, Shen HQ, Zhou YG (2018) Adv Synth Catal 360:1334
244. Guo RN, Gao K, Ye ZS, Shi L, Li Y, Zhou YG (2013) Pure Appl Chem 85:843
245. Ye ZS, Chen MW, Chen QA, Shi L, Duan Y, Zhou YG (2012) Angew Chem Int Ed 51:10181
246. Guo RN, Cai XF, Shi L, Ye ZS, Chen MW, Zhou YG (2013) Chem Commun 49:8537
247. Ji Y, Shi L, Chen MW, Feng GS, Zhou YG (2015) J Am Chem Soc 137:10496
248. Ye ZS, Guo RN, Cai XF, Chen MW, Shi L, Zhou YG (2013) Angew Chem Int Ed 52:3685
249. Chen MW, Ye ZS, Chen ZP, Wu B, Zhou YG (2015) Org Chem Front 2:586
250. Huang WX, Yu CB, Shi L, Zhou YG (2014) Org Lett 16:3324
251. Huang WX, Liu LJ, Wu B, Feng GS, Wang B, Zhou YG (2016) Org Lett 18:3082
252. Hu SB, Chen ZP, Song B, Wang J, Zhou YG (2017) Adv Synth Catal 359:2762
253. Huang WX, Yu CB, Ji Y, Liu LJ, Zhou YG (2016) ACS Catal 6:2368
254. Ji Y, Feng GS, Chen MW, Shi L, Duc H, Zhou YG (2017) Org Chem Front 4:1125
255. Chang M, Huang Y, Liu S, Chen Y, Krska SW, Davies IW, Zhang X (2014) Angew Chem Int
Ed 53:12761
256. Chen MW, Ji Y, Wang J, Chen QA, Shi L, Zhou YG (2017) Org Lett 19:4988
257. Qu B, Mangunuru HPR, Wei X, Fandrick KR, Desrosiers JN, Sieber JD, Kurouski D,
Haddad N, Samankumara LP, Lee H, Savoie J, Ma S, Grinberg N, Sarvestani M, Yee NK,
Song JJ, Senanayake CH (2016) Org Lett 18:4920
258. Qu B, Mangunuru HPR, Tcyrulnikov S, Rivalti D, Zatolochnaya OV, Kurouski D,
Radomkit S, Biswas S, Karyakarte S, Fandrick KR, Sieber JD, Rodriguez S, Desrosiers JN,
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CH (2018) Org Lett 20:1333
259. Chang M, Li W, Zhang X (2011) Angew Chem Int Ed 50:10679
260. Nie H, Zhu Y, Hu X, Wei Z, Yao L, Zhou G, Wang P, Jiang R, Zhang S (2019) Org Lett
21:8641
261. Tang W, Sun Y, Xu L, Wang T, Fan O, Lamc KH, Chan ASC (2010) Org Biomol Chem
8:3464
262. Tang WJ, Tan J, Xu LJ, Lam KH, Fan QH, Chan ASC (2010) Adv Synth Catal 352:1055
263. Xie JH, Yan PC, Zhang QQ, Yuan KX, Zhou QL (2012) ACS Catal 2:561
264. Gao K, Yu CB, Wang DS, Zhou YG (2012) Adv Synth Catal 354:483
265. Feng GS, Zhao ZB, Shi L, Zhou YG (2019) Org Chem Front 6:2250
266. Cartigny D, Nagano T, Ayad T, Genêt JP, Ohshima T, Mashima K, Ratovelomanana-Vidal V
(2010) Adv Synth Catal 352:1886
267. Cartigny D, Berhal F, Nagano T, Phansavath P, Ayad T, Genêt JP, Ohshima T, Mashima K,
Ratovelomanana-Vidal V (2012) J Org Chem 77:4544
268. Nagano T, Iimuro A, Schwenk R, Ohshima T, Kita Y, Togni A, Mashima K (2012) Chem Eur
J 18:11578
269. Higashida K, Nagae H, Mashima K (2016) Adv Synth Catal 358:3949
Iridium-Catalyzed Asymmetric Hydrogenation
203
istamine H1-receptor inverse agonist is commercialized as Zyrtec/Reactine by Pfizer
234. Hou G, Tao R, Sun Y, Zhang X, Gosselin F (2010) J Am Chem Soc 132:2124
235. Kong D, Li M, Zi G, Hou G, He Y (2016) J Org Chem 81:6640
236. Hu XH, Hu XP (2019) Adv Synth Catal 361:5063
237. Mazuela J, Antonsson T, Knerr L, Marsden SP, Munday RH, Johansson MJ (2019) Adv Synth
Catal 361:578
238. Wang WB, Lu SM, Yang PY, Han XW, Zhou YG (2003) J Am Chem Soc 125:10536
239. Yang PY, Zhou YG (2004) Tetrahedron Asymmetry 15:1145
240. Wang DW, Wang XB, Wang DS, Lu SM, Zhou YG, Li YX (2009) J Org Chem 74:2780.
Later, it was shown that an electronically deficient ligand synthesized from (S)-MeO-BiPhep
showed an increase of the activity and enantioselectivity: Zhang DY, Wang DS, Wang MC,
Yu CB, Gao K, Zhou YG (2011) Synthesis 2796
241. Lu SM, Wang YQ, Han XW, Zhou YG (2006) Angew Chem Int Ed 45:2260
242. Shi L, Ye ZS, Cao LL, Guo RN, Hu Y, Zhou YG (2012) Angew Chem Int Ed 51:8286
243. Hu SB, Zhai XY, Shen HQ, Zhou YG (2018) Adv Synth Catal 360:1334
244. Guo RN, Gao K, Ye ZS, Shi L, Li Y, Zhou YG (2013) Pure Appl Chem 85:843
245. Ye ZS, Chen MW, Chen QA, Shi L, Duan Y, Zhou YG (2012) Angew Chem Int Ed 51:10181
246. Guo RN, Cai XF, Shi L, Ye ZS, Chen MW, Zhou YG (2013) Chem Commun 49:8537
247. Ji Y, Shi L, Chen MW, Feng GS, Zhou YG (2015) J Am Chem Soc 137:10496
248. Ye ZS, Guo RN, Cai XF, Chen MW, Shi L, Zhou YG (2013) Angew Chem Int Ed 52:3685
249. Chen MW, Ye ZS, Chen ZP, Wu B, Zhou YG (2015) Org Chem Front 2:586
250. Huang WX, Yu CB, Shi L, Zhou YG (2014) Org Lett 16:3324
251. Huang WX, Liu LJ, Wu B, Feng GS, Wang B, Zhou YG (2016) Org Lett 18:3082
252. Hu SB, Chen ZP, Song B, Wang J, Zhou YG (2017) Adv Synth Catal 359:2762
253. Huang WX, Yu CB, Ji Y, Liu LJ, Zhou YG (2016) ACS Catal 6:2368
254. Ji Y, Feng GS, Chen MW, Shi L, Duc H, Zhou YG (2017) Org Chem Front 4:1125
255. Chang M, Huang Y, Liu S, Chen Y, Krska SW, Davies IW, Zhang X (2014) Angew Chem Int
Ed 53:12761
256. Chen MW, Ji Y, Wang J, Chen QA, Shi L, Zhou YG (2017) Org Lett 19:4988
257. Qu B, Mangunuru HPR, Wei X, Fandrick KR, Desrosiers JN, Sieber JD, Kurouski D,
Haddad N, Samankumara LP, Lee H, Savoie J, Ma S, Grinberg N, Sarvestani M, Yee NK,
Song JJ, Senanayake CH (2016) Org Lett 18:4920
258. Qu B, Mangunuru HPR, Tcyrulnikov S, Rivalti D, Zatolochnaya OV, Kurouski D,
Radomkit S, Biswas S, Karyakarte S, Fandrick KR, Sieber JD, Rodriguez S, Desrosiers JN,
Haddad N, McKellop K, Pennino S, Lee H, Yee NK, Song JJ, Kozlowski MC, Senanayake
CH (2018) Org Lett 20:1333
259. Chang M, Li W, Zhang X (2011) Angew Chem Int Ed 50:10679
260. Nie H, Zhu Y, Hu X, Wei Z, Yao L, Zhou G, Wang P, Jiang R, Zhang S (2019) Org Lett
21:8641
261. Tang W, Sun Y, Xu L, Wang T, Fan O, Lamc KH, Chan ASC (2010) Org Biomol Chem
8:3464
262. Tang WJ, Tan J, Xu LJ, Lam KH, Fan QH, Chan ASC (2010) Adv Synth Catal 352:1055
263. Xie JH, Yan PC, Zhang QQ, Yuan KX, Zhou QL (2012) ACS Catal 2:561
264. Gao K, Yu CB, Wang DS, Zhou YG (2012) Adv Synth Catal 354:483
265. Feng GS, Zhao ZB, Shi L, Zhou YG (2019) Org Chem Front 6:2250
266. Cartigny D, Nagano T, Ayad T, Genêt JP, Ohshima T, Mashima K, Ratovelomanana-Vidal V
(2010) Adv Synth Catal 352:1886
267. Cartigny D, Berhal F, Nagano T, Phansavath P, Ayad T, Genêt JP, Ohshima T, Mashima K,
Ratovelomanana-Vidal V (2012) J Org Chem 77:4544
268. Nagano T, Iimuro A, Schwenk R, Ohshima T, Kita Y, Togni A, Mashima K (2012) Chem Eur
J 18:11578
269. Higashida K, Nagae H, Mashima K (2016) Adv Synth Catal 358:3949
Iridium-Catalyzed Asymmetric Hydrogenation
203