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1
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0035126119
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For recent review for catalytic asymmetric 1,4-addition reaction, see: (a) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171.
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Krause, N.1
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6
-
-
0034817259
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For selected recent examples using oxazolidinone and pyrrolidinone as achiral template in catalytic asymmetric 1,4-addition reactions, see: (b) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480.
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0041878683
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(c) Sibi, M. P.; Manyem, S.; Zimmerman, J. Chem. Rev. 2003, 103, 3263 and references therein.
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(e) Kobayashi, S.; Ogawa, C.; Kawamura, M.; Sugiura, M. Synlett 2001, 983.
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Kobayashi, S.1
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See also ref 4c
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(g) Hird, A. W.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 1276. See also ref 4c.
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(a) Evans, D. A.; Scheidt, K. A.; Fandrick, K. R.; Lam, H.-W.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10780.
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0034006954
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For other applications, see also: (b) Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635.
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For selected examples, see: (a) Sibi, M. P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615.
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19
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0037415096
-
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For other applications, see an excellent review on chiral relay using achiral template: (b) Corminboeuf, O.; Quaranta, L.; Renaud, P.; Liu, M.; Jasperse, C. P.; Sibi, M. P. Chem.-Eur. J. 2003, 9, 28.
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20
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1642535360
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and references therein
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See also: (c) Sibi, M. P.; Ma, Z.-H.; Jasperse, C. P. J. Am. Chem. Soc. 2004, 126, 718 and references therein.
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(e) Sibi, M. P.; Prabagaran, N.; Ghorpade, S. G.; Jasperse, C. P. J. Am. Chem. Soc. 2003, 125, 11796.
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26
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2942692368
-
-
note
-
For imides as substrate, both monodentate and bidentate transition states were proposed, depending on the catalyst and reaction. See ref 6c and e.
-
-
-
-
27
-
-
2942666479
-
-
note
-
2Zn to bidentate substrates with chiral metal catalysts. Appropriate tuning of chiral ligands was necessary. For representative recent examples of catalytic asymmetric 1,4-addition of organozinc reagents, see ref 1a and 2g and references therein.
-
-
-
-
28
-
-
0037420322
-
-
For selected recent examples of 1,4-addition reactions of acyclic α,β-unsaturated ketone from our group, see: (a) Harada, S.; Kumagai, N.; Kinoshita, T.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2582.
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(b) Kumagai, N.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2001, 3, 4251.
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(c) Funabashi, K.; Saida, Y.; Kanai, M.; Arai, T.; Sasai, H.; Shibasaki, M. Tetrahedron Lett., 1998, 39, 7557.
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(d) Yam agiwa, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 16178.
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Epoxidation of α,β-unsaturated ketone: (a) Bougauchi, M.; Watanabe, T.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329.
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(b) Nemoto, T.; Ohshima, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 2725.
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For other examples, see ref 20
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See, also (c) Daikai, K.; Kamaura, M.; Inanaga, J. Tetrahedron Lett. 1998, 39, 7321. For other examples, see ref 20.
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A portion of this article was communicated previously. Kinoshita, T.; Okada, S.; Park, S.-R.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2003, 42, 4680.
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0034654056
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For the synthesis of linked-BINOL 5, see: (a) Matsunaga, S.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252.
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0001304728
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(b) Matsunaga, S.; Ohshima, T.; Shibasaki, M. Adv. Synth. Catal. 2002, 344, 3. Both enantiomers of linked-BINOL are also commercially available from Wako Pure Chemical Industries, Ltd. Catalog No. for (S,S)-5 is No. 152-02431 and (R,R)-5, No. 155-02421.
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45
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0042244168
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and references therein
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(f) Arai, Y.; Kasai, M.; Ueda, K.; Masaki, Y. Synthesis 2003, 1511 and references therein.
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Arai, Y.1
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(a) Evans, D. A.; Borg, G.; Scheidt, K. A.Angew. Chem., Int. Ed. 2002, 41, 3188.
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48
-
-
2942631585
-
-
note
-
Although Arai et al. reported the utility of α,β-unsaturated N-acyt-2-substituted-pyrrole as a Michael acceptor, it might not function as a monodentate substrate because of the coordinating functional group at 2-position. See ref 14e and f.
-
-
-
-
49
-
-
0141618331
-
-
and references therein
-
Ekkati, A. R.; Bates, D. K. Synthesis 2003, 1959 and references therein. The scope of the reaction was limited to aromatic amides and cinnamamide.
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Ekkati, A.R.1
Bates, D.K.2
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51
-
-
2942668666
-
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note
-
Synthesis and application of carbonyldipyrrole 8 was reported by Evans et al. See ref 15a.
-
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53
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(b) Nemoto, T.; Ohshima, T.; Shibasaki, M. J. Synth. Org. Chem. Jpn. 2002, 60, 94.
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Polyamino acid catalysis: (c) Porter, M. J.; Roberts, S. M.; Skidmore, J. Bioorg. Med. Chem. 1999, 7, 2145.
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For selected leading references, see also: (e) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1725.
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63
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3643086474
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See also: (e) Yang, D.; Yip, Y.-C.: Tang, M.-W.; Wong, M.-K.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1996, 118, 491.
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Yang, D.1
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0035955210
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α,β-Unsaturated carboxylic acid imidazolide: (a) Nemoto, T.; Ohshima, T.: Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 9474.
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(b) Ohshima, T.; Nemoto, T.; Tosaki, S.-y.; Kakei, H.; Gnanadesikan, V.; Shibasaki, M. Tetrahedron 2003, 59, 10485.
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Ohshima, T.1
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Shibasaki, M.6
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66
-
-
0037065320
-
-
(a) α,β-Unsaturated amide: Nemoto, T.; Kakei, H.; Gnanadesikan, V.; Tosaki, S.-y.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 14544.
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Nemoto, T.1
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67
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(b) Tosaki, S.-y.; Nemoto, T.; Ohshima, M.; Shibasaki, M. Org. Lett. 2003, 5, 495.
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68
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1842614850
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Application to 1,3-polyol synthesis: (c) Tosaki, S.-y.; Horiuchi, T.; Nemoto, T.; Ohshima, M.; Shibasaki, M. Chem.-Eur. J. 2004, 10, 1527.
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Chem.-Eur. J.
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69
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2942694565
-
-
note
-
3/BINOL complex. Catalyst concentration should be kept low (<5-10 mM) to achieve the best enantioselectivity, because undesired dimeric and oligomeric species would increase under concentrated conditions. See ref 10b for mechanistic studies.
-
-
-
-
70
-
-
2942651167
-
-
note
-
3 was purchased from Kojundo Chemical Laboratory Co., Ltd. (Fax: +81-492-84-1351. sales@kojundo.co.jp).
-
-
-
-
71
-
-
2942677450
-
-
note
-
Reaction time for imidazolide: with 10 mol % of La-BINOL catalyst, at room temperature, 3.5 h, 86% yield and 5 mol % of La-BINOL catalyst, at room temperature, 12 h, 73% yield. Reaction time for amide: 5-10 mol % Sm-BINOL catalyst, at room temperature, 3-24 h, >90% yield. See refs 23 and 24.
-
-
-
-
72
-
-
2942677451
-
-
note
-
With imidazolide or amide as substrate, 5-10 mol % catalyst loading was essential for completion of the reaction.
-
-
-
-
73
-
-
0242713084
-
-
8-BINOL: Terry, T.-L. A.-Y.; Chan, S.-S.; Chan, A. S. C. Adv. Synth. Catal. 2003, 345, 537.
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Adv. Synth. Catal.
, vol.345
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-
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Terry, T.-L.A.-Y.1
Chan, S.-S.2
Chan, A.S.C.3
-
74
-
-
2942668665
-
-
note
-
With less reactive CMHP as oxidant, acid imidazolide resulted in low chemical yield (18 h, 47% yield with 10 mol % catalyst). See ref 23.
-
-
-
-
75
-
-
2942690186
-
-
note
-
8-BINOL catalyst was used, although the reaction did not proceed well with 1 mol % catalyst loading in the case of N-acylimidazole as substrate (section E, Scheme 4).
-
-
-
-
76
-
-
2942679713
-
-
note
-
3 ([Sm-cat] = 0.3 mM), epoxide was obtained in less than 10% yield.
-
-
-
-
77
-
-
2942662293
-
-
note
-
2-urea with base, mCPBA, and aqNaClO with phase-transfer catalyst, either resulted in decompositions of enone or afforded product in low yield (<20%).
-
-
-
-
78
-
-
0037462104
-
-
2Zn/linked-BINOL catalyst, see Mannich-type reaction: (a) Matsunaga, S.; Kumagai, N.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
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Matsunaga, S.1
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79
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0037467125
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Aldol reaction: (b) Kumagai, N.; Matsunaga, S.; Kinoshita, T.; Harada, S.; Okada, S.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2169.
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80
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0000148255
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(c) Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibasaki, M. Org. Lett. 2001, 3, 1539.
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(d) Yoshikawa, N.; Kumagai, N.; Matsunaga, S.; Moll, G.; Ohshima, T.; Suzuki, T.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 2466.
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83
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In addition to the adverse effects of the liberated 4-phenylimidazole, product inhibition by epoxy peroxy ester is also postulated to explain the low reactivity with 1 mol % catalyst (Scheme 4b). Epoxy peroxy ester 21 would function as a bidentate ligand toward the Sm catalyst. Adverse effects of the bidentate coordination were also observed when using an α,β- unsaturated Weinreb amide as a substrate. See ref 24c.
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