SCOPUS 정보 검색 플랫폼

Journal of the American Chemical Society

Volumn 124, Issue 5, 2002, Pages 827-833

The proline-catalyzed direct asymmetric three-component Mannich reaction: Scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohols

(4) List, Benjamin a Pojarliev, Peter a Biller, William T a Martin, Harry J a

a SCRIPPS RESEARCH INSTITUTE (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVE SYNTHESIS;

ALCOHOLS; ALDEHYDES; AMINES; CATALYSIS; KETONES; OPTIMIZATION;

REACTION KINETICS;

1,2 AMINOALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; AMINE; AMINOALCOHOL; CARBONYL DERIVATIVE; KETONE DERIVATIVE; PROLINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; MANNICH REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

ALDEHYDES; AMINES; AMINO ALCOHOLS; CATALYSIS; KETONES; MANNICH BASES; PROLINE; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 0037028550 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja0174231 Document Type: Article

Times cited : (694)

References (81)

1
- 0001144521
- (1828) Ann. Phys. Chem. , vol.12 , pp. 253
- Wöhler, F.¹

2
- 84974853142
- Reviews
- (1912) Arch. Pharm. (Weinheim, Ger.) , vol.250 , pp. 647
- Mannich, C.¹ Krosche, W.²

3
- 0001059120
- Jacobsen, E.N., Pfaltz, A., Yamamoto H., Eds.; Springer: Heidelberg
- (1999) Comprehensive Asymmetric Catalysis , pp. 932-961
- Denmark, S.E.¹ Nicaise, O.J.-C.²

4
- 0000733768
- Trost, B. M., Ed.; Pergamon Press: New York, Chapter 4.1
- (1991) Comprehensive Organic Synthesis , vol.2
- Kleinmann, E.F.¹

5
- 0032482080
- (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 1044-1070
- Arend, M.¹ Westermann, B.² Risch, N.³

6
- 0033534350
- (1999) Tetrahedron Lett. , vol.40 , pp. 307-310
- Yamasaki, S.¹ Iida, T.² Shibaski, M.³

7
- 0033575409
- (1999) Tetrahedron , vol.55 , pp. 8857-8867
- Yamasaki, S.¹ Iida, T.² Shibasaki, M.³

8
- 0034721440
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 9336-9337
- List, B.¹

9
- 0000698759
- (1985) Tetrahedron , vol.41 , pp. 1693-1701
- Kober, R.¹ Papadopoulus, K.² Miltz, W.³ Enders, D.⁴ Steglich, W.⁵ Reuter, H.⁶ Puff, H.⁷

10
- 84986695925
- (1992) Liebigs Ann. Chem. , pp. 233-237
- Risch, N.¹ Esser, A.²

11
- 0031030026
- (1997) Tetrahedron , vol.53 , pp. 689-696
- Vinkovic, V.¹ Sunjic, V.²

12
- 0004036351
- (1998) Eur. Org. Chem. , pp. 197-200
- Zarghi, A.¹ Naimi-Jamal, M.R.² Webb, S.A.³ Saidi, M.R.⁴ Ipaktschi, J.⁵

13
- 0029791647
- (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 981-984
- Enders, D.¹ Ward, D.² Adam, J.³ Raabe, G.⁴

14
- 0038231744
- (2000) Synlett , pp. 644-646
- Enders, D.¹ Oberbörsch, S.² Adam, J.³

15
- 0025895930
- (1991) Tetrahedron Lett. , vol.32 , pp. 5287-5290
- Corey, E.J.¹ Decicco, C.P.² Newbold, R.C.³

16
- 0034678006
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 1063-1065
- Palomo, C.¹ Oiarbide, M.² Gonzalez-Rego, M.C.³ Sharma, A.K.⁴ Garcia, J.M.⁵ Gonzalez, A.⁶ Landa, C.⁷ Linden, A.⁸

17
- 0000882028
- (1987) Chem. Lett. , vol.2 , pp. 293-296
- Yamada, T.¹ Suzuki, H.² Mukaiyama, T.³

18
- 0023250445
- (1987) J. Org. Chem. , vol.52 , pp. 3488-3489
- Shibasaki, M.¹ Ishida, Y.² Iwasaki, G.³ Iimori, T.⁴

19
- 0042406417
- (2000) Chem.-Eur. J. , vol.6 , pp. 2032-2043
- Müller, R.¹ Rottele, H.² Henke, H.³ Waldmann, H.⁴

20
- 0035961112
- (2001) Tetrahedron , vol.57 , pp. 875-887
- Saito, S.¹ Hatanaka, K.² Yamamoto, H.³

21
- 0008026314
- note

22
- 0000656506
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 10520-10524
- Ishihara, K.¹ Miyata, M.² Hattori, K.³ Tada, T.⁴ Yamamoto, H.⁵

23
- 84918184408
- (1984) Helv. Chim. Acta , vol.67 , pp. 1593-1597
- Seebach, D.¹ Betschart, C.² Schiess, M.³

24
- 33745858443
- (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 2422-2423
- Risch, N.¹ Arend, M.²

25
- 0030928524
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 2060-2061
- Fujieda, H.¹ Kanai, M.² Kambara, T.³ Iida, A.⁴ Tomoioka, K.⁵

26
- 0032481071
- (1998) Tetrahedron Lett. , vol.39 , pp. 9055-9058
- Kambara, T.¹ Hussein, M.A.² Fujieda, H.³ Iida, A.⁴ Tomioka, K.⁵

27
- 0033591004
- (1999) Chem. Commun. , pp. 715-716
- Tomioka, K.¹ Fujieda, H.² Hayashi, S.³ Hussein, M.A.⁴ Kambara, T.⁵ Nomura, Y.⁶ Motomu, K.⁷ Koga, K.⁸

28
- 0033040001
- (1999) Chem. Pharm. Bull. , vol.47 , pp. 720-721
- Kambara, T.¹ Tomioka, K.²

29
- 0033543491
- (1999) Tetrahedron , vol.55 , pp. 11219-11228
- Hussein, M.A.¹ Iida, A.² Tomioka, K.³

30
- 0030788354
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 7153-7154
- Ishitani, H.¹ Ueno, M.² Kobayashi, S.³

31
- 0032554058
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 431-432
- Kobayashi, S.¹ Ishitani, H.² Ueno, M.³

32
- 0034734313
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 8180-8186
- Ishitani, H.¹ Ueno, M.² Kobayashi, S.³

33
- 0032542749
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 2474-2475
- Hagiwara, E.¹ Fujii, A.² Soeoka, M.³

34
- 0033575073
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 5450-5458
- Fujii, A.¹ Hagiwara, E.² Sodeoka, M.³

35
- 0001209391
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 4548-4549
- Ferraris, D.¹ Young, B.² Dudding, T.³ Lectka, T.⁴

36
- 0000603617
- (1998) J. Org. Chem. , vol.63 , pp. 6090-6091
- Ferraris, D.¹ Young, B.² Cox, C.³ Drury III, W.J.⁴ Lectka, T.⁵

37
- 0033515594
- (1999) J. Org. Chem. , vol.64 , pp. 2168-2169
- Ferraris, D.¹ Dudding, T.² Young, B.³ Drury III, W.J.⁴ Lectka, T.⁵

38
- 0035907791
- (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2271-2274
- Xue, S.¹ Yu, S.² Deng, Y.³ Wulff, W.D.⁴

39
- 0033579639
- (1999) Tetrahedron Lett. , vol.40 , pp. 8949-8953
- Martin, S.F.¹ Lopes, O.D.²

40
- 0035902842
- (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2995-2997
- Juhl, K.¹ Gathergood, N.² Jørgensen, K.A.³

41
- 0008120804
- Asymmetric Synthesis of Optically Active Polycyclic Organic Compounds. German Patent DE 2102623, Jul 29, 1971
- Hajos, Z.G.¹ Parrish, D.R.²

42
- 0008075532
- Optically Active 1,5-Indanone and 1,6-Naphthalenedione. German Patent DE 2014757, Oct 7, 1971
- Eder, U.¹ Sauer, G.² Wiechert, R.³

43
- 84981886574
- (1971) Angew. Chem., Int. Ed. Engl. , vol.10 , pp. 496
- Eder, U.¹ Sauer, G.² Wiechert, R.³

44
- 33847804003
- (1974) J. Org. Chem. , vol.39 , pp. 1615
- Hajos, Z.G.¹ Parrish, D.R.²

45
- 0034654216
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 2395-2396
- List, B.¹ Lerner, R.A.² Barbas III, C.F.³

46
- 0034596299
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 7386-7387
- Notz, W.¹ List, B.²

47
- 0035932079
- (2001) Org. Lett. , vol.3 , pp. 573-575
- List, B.¹ Pojarliev, P.² Castello, C.³

48
- 0034750244
- (2001) Synlett. , pp. 1675-1686
- List, B.¹

49
- 0030820620
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 6452-6453
- Evans, D.A.¹ Nelson, S.G.²

50
- 0000761777
- (2001) Org. Lett. , vol.3 , pp. 2423-2425
- List, B.¹ Pojarliev, P.² Martin, H.J.³

51
- 0034748990
- (2001) Synlett , pp. 1687-1689
- List, B.¹ Castello, C.²

52
- 0001549125
- (1999) Org. Lett. , vol.1 , pp. 1965-1967
- Manabe, K.¹ Kobayashi, S.²

53
- 0008116941
- note

54
- 0008152274
- note

55
- 0035825097
- (2001) Tetrahedron Lett. , vol.42 , pp. 199-201
- Notz, W.¹ Sakthivel, K.² Bui, T.³ Zhong, G.⁴ Barbas III, C.F.⁵

56
- 0034823456
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 3367-3368
- Trost, B.M.¹ Ito, H.² Silcoff, E.R.³

57
- 0034697199
- (2000) Tetrahedron , vol.56 , pp. 2561-2576
- Bergmeier, S.C.¹

58
- 33748233248
- (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 451-454
- Li, G.¹ Chang, H.-T.² Sharpless, K.B.³

59
- 0033083525
- (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 326-329
- O'Brien, P.¹

60
- 0344137670
- (1991) J. Org. Chem. , vol.56 , pp. 2499-2506
- Van Draanen, N.A.¹ Arseniyadis, S.² Crimmins, M.T.³ Heathcock, C.H.⁴

61
- 0008071169
- note

62
- 0001259941
- and references therein
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 2581-2589
- Ziegler, F.E.¹ Metcalf III, C.A.² Nangia, A.³ Schulte, G.⁴

63
- 0002858266
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 1207-1217
- Reddy, K.L.¹ Sharpless, K.B.²

64
- 33748666004
- (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 2519-2526
- O'Brien, P.¹ Osborne, S.A.² Parker, D.D.³

65
- 0000312046
- (1985) Org. Synth. , vol.63 , pp. 136-139
- Smith, G.A.¹ Gawley, R.E.²

66
- 3242697074
- (1993) J. Org. Chem. , vol.58 , pp. 3568-3571
- Meyers, A.I.¹ McKennon, M.J.²

67
- 33748838173
- (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 1219-1222
- Enders, D.¹ Reinhold, U.²

68
- 0001850963
- (1996) Liebigs Ann. , pp. 11-26
- Enders, D.¹ Reinhold, U.²

69
- 0035843416
- (2001) Tetrahedron Lett. , vol.42 , pp. 2051-2054
- Barrow, J.C.¹ Ngo, P.L.² Pellicore, J.M.³ Selnick, H.G.⁴ Nantermet, P.G.⁵

70
- 0343091511
- (2000) Chirality , vol.12 , pp. 404-407
- Youn, S.W.¹ Choi, J.Y.² Kim, Y.H.³

71
- 0035932587
- (2001) Org. Lett. , vol.3 , pp. 897-899
- Morita, T.¹ Nagasawa, Y.² Yahiro, S.³ Matsunaga, H.⁴ Kunieda, T.⁵

72
- 0031019640
- (1997) Tetrahedron , vol.53 , pp. 1275-1294
- Matsunaga, H.¹ Ishizuka, T.² Kunieda, T.³

73
- 0032540412
- (1998) J. Org. Chem. , vol.63 , pp. 2742-2748
- Takacs, J.M.¹ Jaber, M.R.² Vellekoop, A.S.³

74
- 0008027312
- note

75
- 0002801544
- (1937) J. Am. Chem. Soc. , vol.59 , pp. 96
- Hammet, L.P.¹

76
- 24244439460
- (1953) Chem. Rev. , vol.53 , pp. 1-261
- Jaffe, H.H.¹

77
- 0033583015
- (1999) Tetrahedron , vol.55 , pp. 3605-3614
- Kitamura, M.¹ Oka, H.² Noyori, R.³

78
- 79958222806
- (1981) Helv. Chim. Acta , vol.64 , pp. 1413-1423
- Seebach, D.¹ Golinski, J.²

79
- 0035903586
- (2001) Angew. Chem., Int. Ed. , vol.30 , pp. 3337-3340
- Hoffmann, R.¹

80
- 0008025774
- (1974) J. Chem. Soc., Perkin Trans. 2 , pp. 1081-1084
- Bjoergo, J.¹ Boyd, D.R.² Watson, C.G.³ Jennings, W.B.⁴ Jerina, D.M.⁵

81
- 0001497360
- (1974) Tetrahedron , vol.30 , pp. 1861-1870
- Kessler, H.¹

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