SCOPUS 정보 검색 플랫폼

Journal of the American Chemical Society

Volumn 124, Issue 1, 2002, Pages 67-77

Catalytic, enantioselective alkylation of α-imino esters: The synthesis of nonnatural α-amino acid derivatives

(8) Ferraris, D a Young, B a Cox, C a Dudding, T a Drury III, W J a Ryzhkov, L b Taggi, A E a Lectka, T a

a JOHNS HOPKINS UNIVERSITY (United States)

b TOWSON UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY;

ALKYLATION; AMINO ACIDS; CATALYSIS; CATALYSTS; OLEFINS; REACTION KINETICS; SILANES; SYNTHESIS (CHEMICAL); TRANSITION METALS;

ESTERS;

ACETAL DERIVATIVE; ALKENE DERIVATIVE; ALLYL COMPOUND; ALPHA AMINO ACID; AMINO ACID DERIVATIVE; ESTER DERIVATIVE; KETENE DERIVATIVE; PHOSPHINE DERIVATIVE; SILANE DERIVATIVE;

ALKYLATION; AMINO ACID ANALYSIS; AMINO ACID SYNTHESIS; ARTICLE; CATALYSIS; CHEMICAL REACTION; DIASTEREOISOMER; ENANTIOMER; STEREOCHEMISTRY; STEREOSPECIFICITY;

ACETALS; ALKYLATION; AMINO ACIDS; CATALYSIS; ESTERS; IMINO ACIDS; STEREOISOMERISM;

EID: 0037045227 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja016838j Document Type: Article

Times cited : (189)

References (121)

1
- 0038106171
- (1998) Chem. Rev. , vol.98 , pp. 1407
- Bloch, R.¹

2
- 0003416748
- Pergammon: New York
- (1989) Synthesis of Optically Active α-Amino Acids
- Williams, R.M.¹

3
- 0028355337
- (1994) Tetrahedron , vol.50 , pp. 1539
- Duthaler, R.O.¹

4
- 0001313865
- (1995) Acc. Chem. Res. , vol.28 , pp. 299
- Hegedus, L.¹

5
- 0028097524
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 8544
- Boger, D.L.¹ Patane, M.A.² Zhou, J.³

6
- 0025647383
- (1990) J. Org. Chem. , vol.55 , pp. 6000
- Boger, D.L.¹ Yohannes, D.²

7
- 0000862669
- (1999) Chem. Rev. , vol.99 , pp. 1069
- Kobayashi, S.¹ Ishitiani, H.²

8
- 0032542749
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 2474
- Hagiwara, E.¹ Fujii, A.² Sodeoka, M.³

9
- 0030669813
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 10049
- Kobayashi, S.¹ Nagayama, S.²

10
- 0030788354
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 7153
- Ishitani, H.¹ Ueno, M.² Kobayashi, S.³

11
- 0034721440
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 9336
- List, B.¹

12
- 0032486806
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 7649
- Gomez-Bengoa, E.¹ Heron, N.M.² Didiuk, M.T.³ Luchaco, C.A.⁴ Hoveyda, A.H.⁵

13
- 85077901656
- (1984) Synthesis , pp. 85
- Zaugg, H.E.¹

14
- 85077839579
- (1984) Synthesis , pp. 181
- Zaugg, H.E.¹

15
- 0035793657
- (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 875
- Yet, L.¹

16
- 0034599654
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 1279
- Sigman, M.S.¹ Vachal, P.² Jacobsen, E.N.³

17
- 0034701211
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 2657
- Porter, J.R.¹ Wirschun, W.G.² Kuntz, K.W.³ Snapper, M.L.⁴ Hoveyda, A.H.⁵

18
- 0003554758
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 4901
- Sigman, M.S.¹ Jacobsen, E.N.²

19
- 0032554058
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 431
- Kobayashi, S.¹ Ishitani, H.² Ueno, M.³

20
- 0030928524
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 2060
- Fujieda, H.¹ Kanai, M.² Kambara, T.³ Iida, A.⁴ Tomioka, K.⁵

21
- 0002487883
- (1997) Top. Curr. Chem. , vol.190 , pp. 131
- Weinreb, S.M.¹

22
- 0001209391
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 4548
- Ferraris, D.¹ Young, B.² Dudding, T.³ Lectka, T.⁴

23
- 0000603617
- (1998) J. Org. Chem. , vol.63 , pp. 6090
- Ferraris, D.¹ Young, B.² Cox, C.³ Drury III, W.J.⁴ Dudding, T.⁵ Lectka, T.⁶

24
- 0034680630
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 4114
- Saaby, S.¹ Fang, X.² Gathergood, N.³ Jørgensen, K.A.⁴

25
- 0034675619
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3558
- Jørgensen, K.A.¹

26
- 0034600913
- (2000) Chem. Chetn. Eur. J. , vol.6 , pp. 2435
- Yao, S.¹ Saaby, S.² Hazell, R.G.³ Jørgensen, K.A.⁴

27
- 0032556461
- (1998) J. Chem. Soc., Chem. Commun. , pp. 2547
- Yao, S.¹ Fang, X.² Jørgensen, K.A.³

28
- 0033515594
- (1999) J. Org. Chem. , vol.64 , pp. 2168
- Ferraris, D.¹ Dudding, T.² Young, B.³ Drury III, W.J.⁴ Lectka, T.⁵

29
- 0032576117
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 11006
- Drury III, W.J.¹ Ferraris, D.² Cox, C.³ Young, B.⁴ Lectka, T.⁵

30
- 0028952646
- (1995) Synthesis , pp. 347
- Borzilleri, R.B.¹ Weinreb, S.M.²

31
- 6744264109
- (1992) Chem. Rev. , vol.92 , pp. 1021
- Mikami, K.¹ Shimizu, M.²

32
- 0032540647
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 5824
- Evans, D.A.¹ Burgey, C.S.² Paras, N.A.³ Vojkovsky, T.⁴ Tregay, S.W.⁵

33
- 0000218981
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 1940
- Mikami, K.¹ Terada, M.² Nakai, T.³

34
- 0033559915
- (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 825
- Chen, G.-M.¹ Ramachandran, P.V.² Brown, H.C.³

35
- 0000298478
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 4242
- Nakamura, H.¹ Nakamura, K.² Yamamoto, Y.³

36
- 0029895814
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 4723
- Yanagisawa, A.¹ Nakashima, H.² Ishiba, A.³ Yamamoto, H.⁴

37
- 0033603563
- (1999) J. Org. Chem. , vol.64 , pp. 4844
- Fang, X.¹ Johannsen, M.² Yao, S.³ Gathergood, N.⁴ Hazell, R.G.⁵ Jørgensen, K.A.⁶

38
- 0001388951
- (1984) J. Org. Chem. , vol.49 , pp. 5058
- Tschaen, D.H.¹ Turos, E.² Weinreb, S.M.³

39
- 0029895814
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 4723
- Yanagisawa, A.¹ Nakashima, H.² Ishiba, A.³ Yamamoto, H.⁴

40
- 0001846018
- Shriver, D. F., Ed.; Plenum: New York
- (1979) Inorganic Synthesis , vol.19 , pp. 90
- Kubas, G.J.¹

41
- 0345195964
- (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 3124
- Pagenkopf, B.L.¹ Krüger, J.² Stojanovic, A.³ Carreira, E.M.⁴

42
- 0038475549
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 837
- Kruger, J.¹ Carreira, E.M.²

43
- 0031434549
- (1997) J. Med. Chem. , vol.40 , pp. 4378
- Rover, S.¹ Cesura, A.M.² Huguenin, P.³ Kettler, R.⁴ Szente, A.⁵

44
- 0030592758
- (1996) Tetrahedron , vol.52 , pp. 14757
- Golubev, A.S.¹ Sewald, N.² Bürger, K.³

45
- 0030024339
- (1996) J. Org. Chem. , vol.61 , pp. 715
- Berrée, F.¹ Chang, K.² Cobas, A.³ Rapoport, H.⁴

46
- 0029497024
- (1995) Chem. Soc. Rev. , pp. 401
- Botting, N.P.¹

47
- 0028343956
- (1994) J. Med. Chem. , vol.37 , pp. 647
- Pellicciari, R.¹ Natalini, B.² Constantino, G.³

48
- 0030215491
- (1996) Acta Chem. Scand. , vol.50 , pp. 649
- Li, G.¹ Sharpless, K.B.²

49
- 0033575073
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 5450
- Fujii, A.¹ Hagiwara, E.² Sodeoka, M.³

50
- 0003625968
- Wilkinson, G., Fillard, R. D., McCleverty, J. A., Eds.; Pergamon: New York
- (1987) Comprehensive Coordination Chemistry , vol.5
- Hathaway, B.J.¹

51
- 0011404010
- (1986) J. Org. Chem. , vol.51 , pp. 629
- Tayaka, H.¹ Mashima, K.² Koyano, K.³ Yagi, M.⁴ Kumobayashi, H.⁵ Taketomi, T.⁶ Akutagawa, S.⁷ Noyori, R.⁸

52
- 2042457903
- note

53
- 33845281512
- (1987) Inorg. Chem. , vol.26 , pp. 3383
- Berners-Price, S.J.¹ Johnson, R.K.² Mirabelli, C.K.³ Faucette, L.F.⁴ McCabe, F.L.⁵ Sadler, P.J.⁶

54
- 0030583074
- (1996) J. Organomet. Chem. , vol.516 , pp. 235
- Abu-Gnim, C.¹ Amer, I.²

55
- 37049084931
- (1987) J. Chem. Soc., Chem. Commun. , pp. 1891
- Wegman, R.W.¹ Abatjoglou, A.G.² Harrison, A.M.³

56
- 0001571273
- (1987) J. Organomet. Chem. , vol.319 , pp. 285
- Van Vliet, R.P.¹ Van Koten, G.² Modder, J.F.³ Van Beek, J.A.M.⁴ Klaver, W.J.⁵

57
- 0345491105
- (1988) Phys. Rev. B: Condens. Matter , vol.37 , pp. 785
- Lee, C.¹ Yang, W.² Parr, R.G.³

58
- 0000189651
- (1993) J. Chem. Phys. , vol.98 , pp. 5648
- Becke, A.D.¹

59
- 34250817103
- (1993) J. Chem. Phys. , vol.98 , pp. 1372
- Becke, A.D.¹

60
- 0004009372
- Wiley-Interscience: New York
- (1988) Advanced Inorganic Chemistry , pp. 756
- Cotton, F.A.¹ Wilkinson, G.²

61
- 2042491533
- note

62
- 2042520395
- note

63
- 0001013874
- (1987) Chem. Lett. , pp. 491
- Mukayama, T.¹ Kobayashi, S.² Tamura, M.³ Sagawa, Y.⁴

64
- 2042450283
- (1985) Chem. Lett. , vol.447
- Mukaiyama, T.¹ Kobayashi, S.² Murakami, M.³

65
- 0347195435
- (1980) J. Org. Chem. , vol.45 , pp. 1066
- Heathcock, C.H.¹ Buse, C.T.² Kleschick, W.A.³ Pirrung, M.C.⁴ Sohn, J.E.⁵ Lampe, J.⁶

66
- 0031437775
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 12004
- Ruthkosky, M.¹ Kelly, C.A.² Zaros, M.C.³ Meyer, G.J.⁴

67
- 0000076280
- (1975) Tetrahedron , vol.31 , pp. 2363
- Barza, S.¹ Hoffman, C.W.²

68
- 0007618938
- Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: New York
- (1995) Comprehensive Organic Functional Group Transformations , vol.1 , pp. 447
- Hayes, M.A.¹

69
- 0000991875
- (1992) J. Org. Chem. , vol.57 , pp. 2034
- Mukai, C.¹ Miyakawa, M.² Mihira, A.³ Hanaoka, M.⁴

70
- 0026080854
- (1991) Tetrahedron , vol.47 , pp. 3007
- Mukai, C.¹ Cho, W.-J.² Kim, I.J.³ Hanaoka, M.⁴

71
- 0030976603
- (1997) Tetrahedron Lett. , vol.38 , pp. 3059
- Gair, S.¹ Jackson, R.F.W.² Brown, P.A.³

72
- 0027383857
- (1993) J. Org. Chem. , vol.58 , pp. 5972
- Barluenga, J.¹ Viado, A.L.² Aguilar, E.³ Fustero, S.⁴ Olano, B.⁵

73
- 37049067145
- (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 1719
- Jackson, R.F.W.¹ Rettie, A.B.² Wood, A.³ Wythes, M.J.⁴

74
- 0021202331
- (1984) J. Org. Chem. , vol.49 , pp. 2714
- Raffauf, R.F.¹ Zennie, T.M.² Onan, K.D.³ LeQuesne, P.W.⁴

75
- 0026071725
- (1991) J. Org. Chem. , vol.56 , pp. 1894
- Barrett, A.G.M.¹ Dhanak, D.² Lebold, S.³ Russell, M.A.⁴

76
- 0023889588
- (1988) J. Org. Chem. , vol.53 , pp. 1298
- Helms, G.L.¹ Moore, R.E.² Niemzura, W.P.³ Patterson, G.M.L.⁴ Tomer, K.B.⁵ Gross, M.L.⁶

77
- 2042531264
- note

78
- 84989525764
- (1987) Synthesis , pp. 223
- Münster, P.¹ Steglich, W.²

79
- 84985239895
- (1983) Liebigs Ann. Chem. , pp. 599
- Kober, R.¹ Steglich, W.²

80
- 33845278130
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 1547
- Williams, R.M.¹ Sinclair, P.J.² Zhai, D.³ Chen, D.⁴

81
- 0007618939
- (1996) Monatsh. Chem. , vol.127 , pp. 1291
- Matuszczak, B.¹

82
- 0030869889
- (1997) Tetrahedron , vol.53 , pp. 15787
- Bowman, W.R.¹ Coghlan, D.R.²

83
- 0025143818
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 3475
- Garigipati, R.S.¹ Tschaen, D.M.² Weinreb, S.M.³

84
- 0000120488
- (1986) Tetrahedron Lett. , vol.42 , pp. 2099
- Weinreb, S.M.¹ Demko, D.M.² Lessen, T.A.³

85
- 33845550921
- (1983) J. Org. Chem. , vol.48 , pp. 366
- Kosikowski, A.P.¹ Adamczyk, M.²

86
- 0028202744
- (1994) J. Med. Chem. , vol.37 , pp. 334
- Salituro, F.¹ Tomlinson, R.C.² Baron, B.M.³ Palfreyman, M.G.⁴ McDonald, I.A.⁵

87
- 0026515334
- (1992) Chem. Pharm. Bull. , vol.40 , pp. 12
- Kita, Y.¹ Shibata, N.² Miki, T.³ Takemura, Y.⁴ Tamura, O.⁵

88
- 0000986488
- (1989) Tetrahedron Lett. , vol.30 , pp. 747
- Onaka, M.¹ Ohno, R.² Izumi, Y.³

89
- 0000117596
- (1954) J. Am. Chem. Soc. , vol.76 , pp. 3408
- Grubb, W.T.¹

90
- 0032556461
- (1998) J. Chem. Soc., Chem. Commun. , pp. 2547
- Yao, S.¹ Fang, X.² Jørgensen, K.A.³

91
- 2042532952
- note

92
- 0001533216
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 5545
- Tabushi, I.¹ Kuroda, Y.² Yamada, M.³ Higashimura, H.⁴

93
- 0001620284
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 7354
- Gebler, J.¹ Woodside, A.B.² Poulter, C.D.³

94
- 0019129934
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 4267
- Gerig, J.T.¹ Klinkenborg, J.C.²

95
- 0027419617
- (1993) Tetrahedron Lett. , vol.34 , pp. 1057
- Sakagami, Y.¹ Manabe, K.² Aitani, T.³ Thiruvikraman, S.V.⁴ Marumo, S.⁵

96
- 0033523812
- (1999) Org. Lett. , vol.1 , pp. 1443
- Elder, A.M.¹ Rich, D.H.²

97
- 0027320379
- (1993) Tetrahedron Lett. , vol.34 , pp. 5221
- Miles, W.H.¹ Berreth, C.L.² Smiley, P.M.³

98
- 0031776141
- (1998) Synthesis , vol.61 , pp. 509
- Weinreb, S.M.¹ Smith, D.T.² Jin, J.³

99
- 2042452774
- (1996) J. Org. Chem. , vol.61 , pp. 9
- Laschat, S.¹ Fröhlich, R.² Wibbeling, B.³

100
- 84989457263
- (1994) Chem. Ber. , vol.127 , pp. 2023
- Laschat, S.¹ Grehl, M.²

101
- 33748812457
- (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 458
- Laschat, S.¹ Grehl, M.²

102
- 0027218158
- (1993) Tetrahedron Lett. , vol.34 , pp. 4841
- Mikami, K.¹ Kaneko, M.² Yajima, T.³

103
- 0001388951
- (1984) J. Org. Chem. , vol.49 , pp. 5058
- Tschaen, D.M.¹ Turos, E.² Weinreb, S.M.³

104
- 0000841502
- (1982) Tetrahedron Lett. , vol.23 , pp. 3015
- Tschaen, D.M.¹ Weinreb, S.M.²

105
- 0030741435
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 5774
- Jin, J.¹ Weinreb, S.M.²

106
- 0032474797
- (1998) Tetrahedron , vol.54 , pp. 7907
- Tanner, D.¹ Hagberg, L.²

107
- 0035912368
- (2001) Org. Lett. , vol.3 , pp. 1233
- Koh, J.H.¹ Larsen, A.O.² Gagné, M.R.³

108
- 0004018410
- VCH: Weinheim
- (1988) Solvents and Solvent Effects in Organic Chemistry, 2nd ed. , pp. 164-165
- Reichardt, C.¹

109
- 2042455336
- (1980) J. Org. Chem. , vol.45 , pp. 4
- Achmatowicz O., Jr.¹ Szymoniak, J.²

110
- 0007653714
- (1982) J. Org. Chem. , vol.47 , pp. 3355
- Kwart, H.¹ Brechbiel, M.W.²

111
- 0001120647
- (1972) J. Am. Chem. Soc. , vol.94 , pp. 3953
- Dai, S.-H.¹ Dolbier W.R., Jr.²

112
- 0004024904
- Wiley: New York
- (1984) Determination of Organic Reaction Mechanisms , pp. 83-111
- Carpenter, B.K.¹

113
- 0004165224
- Harper and Row: New York
- (1987) Chemical Kinetics
- Laidler, K.J.¹

114
- 0001045470
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 4083
- Kobayashi, S.¹ Ishitani, H.²

115
- 0033559915
- (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 825
- Chen, G.-M.¹ Ramachandran, P.V.² Brown, H.C.³

116
- 0000298478
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 4242
- Nakamura, H.¹ Nakamura, K.² Yamamoto, Y.³

117
- 0033574380
- (1998) J. Org. Chem. , vol.64 , pp. 2614
- Nakamura, K.¹ Nakamura, H.² Yamamoto, Y.³

118
- 0029895814
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 4723
- Yanagisawa, A.¹ Nakashima, H.² Ishiba, A.³ Yamamoto, H.⁴

119
- 0033574553
- (1999) Tetrahedron Lett. , vol.40 , pp. 3093
- Burk, M.J.¹ Bedingfield, K.M.² Kiesman, W.F.³

120
- 0001217267
- (1980) Tetrahedron Lett. , vol.21 , pp. 3915
- Hayashi, T.¹ Katsuro, Y.² Kumada, M.³

121
- 0000563950
- (1986) J. Org. Chem. , vol.51 , pp. 3213
- Viski, P.¹ Szeverényi, Z.² Simándi, L.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.