SCOPUS 정보 검색 플랫폼

Journal of the American Chemical Society

Volumn 123, Issue 45, 2001, Pages 11273-11283

Transition states of amine-catalyzed aldol reactions involving enamine intermediates- theoretical studies of mechanism, reactivity, and stereoselectivity

(2) Bahmanyar, S a Houk, K N a

a UNIVERSITY OF CALIFORNIA (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TRANSITION STATES;

ACTIVATION ENERGY; ALDEHYDES; AMINES; HYDROGEN BONDS; KETONES; PROBABILITY DENSITY FUNCTION;

STEREOCHEMISTRY;

AMINE; ENAMINE;

ARTICLE; CHEMICAL REACTION; ORGANIC CHEMISTRY; PHASE TRANSITION; SOLVATION; STEREOCHEMISTRY; SYNTHESIS;

ACETALDEHYDE; ALDEHYDES; AMINES; CATALYSIS; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM; SUBSTRATE SPECIFICITY; THERMODYNAMICS; VINYL COMPOUNDS;

EID: 0035860999 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja011403h Document Type: Article

Times cited : (345)

References (65)

1
- 0003458662
- Pergamon: Oxford and references therein
- (1994) Enzymes in Synthetic Organic Chemistry
- Wong, C.-H.¹ Whitesides, G.M.²

2
- 0002418079
- and references therein
- (1996) Top. Curr. Chem. , vol.184 , pp. 98-183
- Fessner, W.-D.¹ Walter, C.²

3
- 0034678591
- and references therein
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 1352-1374
- Machajewski, T.D.¹ Wong, C.-H.²

4
- 0029590066
- (1995) Science , vol.270 , pp. 1797-1800
- Wagner, J.¹ Lerner, R.A.² Barbas II, C.F.³

5
- 0031457319
- (1997) Science , vol.278 , pp. 2085-2092
- Barbas III, C.F.¹ Heine, A.² Zhong, G.³ Hoffmann, T.⁴ Gramatikova, S.⁵ Björnestedt, R.⁶ List, B.⁷ Anderson, J.⁸ Stura, E.A.⁹ Wilson, I.A.¹⁰ Lerner, R.A.¹¹

6
- 0032054562
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 2768-2779
- Hoffmann, T.¹ Zhong, G.² List, B.³ Shabat, D.⁴ Anderson, J.⁵ Gramatikova, S.⁶ Lerner, R.A.⁷ Barbas III, C.F.⁸

7
- 0030767734
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 8131-8132
- Zhong, G.¹ Hoffmann, T.² Lerner, R.A.³ Danishefsky, S.⁴ Barbas III, C.F.⁵

8
- 0033581769
- (1999) Org. Lett. , vol.1 , pp. 1623-1626
- List, B.¹ Lerner, R.A.² Barbas III, C.F.³

9
- 0006528614
- Asymmetric Synthesis of Optically Active Polycyclic Organic Compounds. German Patent DE2102623, Jul 29, 1971
- Hajos, Z.G.¹ Parrish, D.R.²

10
- 0015893142
- (1973) J. Org. Chem. , vol.38 , pp. 3239-3243
- Hajos, Z.G.¹ Parrish, D.R.²

11
- 33847804003
- (1974) J. Org. Chem. , vol.39 , pp. 1615-1621
- Hajos, Z.G.¹ Parrish, D.R.²

12
- 0006596122
- Perhydroin-l,5-diones and 1,06-Tetralindiones. U.S. Patent 3975440, Aug 17, 1976 (Assignee: Hoffmann-La Roche Inc., Nutley, NJ 07110)
- Hajos, Z.G.¹ Parrish, D.R.²

13
- 0006528066
- Optically active 1,5-Indanone and 1,6-Napthalenedione. German Patent DE 2014757, Oct 7, 1971
- Eder, U.¹ Sauer, G.² Wiechert, R.³ Schering, A.-G.⁴

14
- 84981886574
- (1971) Angew. Chem., Int. Ed. Engl. , vol.10 , pp. 496-497
- Eder, U.¹ Sauer, G.² Wiechert, R.³

15
- 0034654216
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 2395-2396
- List, B.¹ Lerner, R.A.² Barbas III, C.F.³

16
- 0034596299
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 7386-7387
- Notz, W.¹ List, B.²

17
- 0035932079
- (2001) Org. Lett. , vol.3 , pp. 573-575
- List, B.¹ Pojarliev, P.² Castello, C.³

18
- 0006528330
- Private communication
- List, B.¹

19
- 0034812506
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 5260-5267
- Sakthivel, K.¹ Notz, W.² Bui, T.³ Barbas III, C.F.⁴

20
- 0001463016
- (1995) J. Org. Chem. , vol.60 , pp. 6970-6979
- Reymond, J.L.¹ Chen, Y.²

21
- 0032530490
- and references therein
- (1998) J. Mol. Catal. B.: Enzymatic , vol.5 , pp. 331-337
- Reymond, J.L.¹

22
- 0001748275
- (1965) Tetrahedron Lett. , vol.43 , pp. 3785-3793
- Spencer, T.A.¹ Neel, H.S.² Flechtner, T.W.³ Zayle, R.A.⁴

23
- 0000848939
- (1963) J. Am. Chem. Soc. , vol.85 , pp. 3785-3793
- Spencer, T.A.¹ Schmiegel, K.K.² Williamson, K.L.³

24
- 0017156419
- (1976) J. Am. Chem. Soc. , vol.98 , pp. 4975-4982
- Danishefsky, S.¹ Cain, P.²

25
- 0034596452
- (2000) Tetrahedron Lett. , vol.41 , pp. 6951-6954
- Barbas III, C.F.¹ Bui, T.²

26
- 0028948656
- (1995) J. Org. Chem. , vol.60 , pp. 1114-1115
- Bruner, S.D.¹ Radeke, H.S.² Tallarico, J.A.³ Snapper, M.L.⁴

27
- 0016700132
- (1975) Chem. Pharm. Bull. , vol.23 , pp. 1103-1109
- Hiroi, K.¹ Yamada, S.I.²

28
- 49249152530
- (1979) Tetrahedron Lett. , vol.36 , pp. 3469-3472
- Terashima, S.¹ Satu, S.² Koga, K.³

29
- 0000246845
- (1988) Bull. Soc. Chim. Fr. , pp. 499-507
- Agami, C.¹

30
- 37049096201
- (1984) J. Chem. Soc., Chem. Commun. , vol.7 , pp. 418-420
- Agami, C.¹ Levisalles, J.² Sevestre, H.³

31
- 0006583862
- (1987) J. Org. Chem. , vol.52 , pp. 5611-5615
- Sevin, A.¹ Maddaluno, J.² Agami, C.³

32
- 84987467086
- (1990) Helv. Chim. Acta , vol.73 , pp. 552-573
- Sevin, A.¹ Masure, D.² Geissner-Prettre, C.³

33
- 0001673924
- (1998) Tetrahedron: Asymmetry , vol.9 , pp. 1059-1064
- Tran Huu Dau, M.E.¹ Riche, C.² Dumas, F.³ D'Angelo, J.⁴

34
- 0001197645
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 6947-6953
- Loncharich, R.J.¹ Houk, K.N.²

35
- 0001152307
- (1992) J. Org. Chem. , vol.57 , pp. 1354-1361
- Thomas, B.E.¹ Loncharich, R.J.² Houk, K.N.³

36
- 0001166005
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 790
- Thomas, B.E.¹ Houk, K.N.²

37
- 0031040549
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 826-827
- Lucero, M.J.¹ Houk, K.N.²

38
- 34250817103
- (1993) J. Chem. Phys. , vol.98 , pp. 1372-1377
- Becke, A.D.¹

39
- 0000189651
- (1993) J. Chem. Phys. , vol.98 , pp. 5648-5652
- Becke, A.D.¹

40
- 0345491105
- (1988) Phys. Rev. B , vol.37 , pp. 785-789
- Lee, C.¹ Yang, W.² Parr, R.G.³

41
- 36849115659
- (1971) J. Chem. Phys. , vol.54 , pp. 724-728
- Ditchfield, R.¹ Hehre, W.J.² Pople, J.A.³

42
- 0347170005
- (1972) J. Chem. Phys. , vol.56 , pp. 2257-2261
- Hehre, W.J.¹ Ditchfield, R.² Pople, J.A.³

43
- 33748545144
- (1973) Theor. Chim. Acta , vol.28 , pp. 213-222
- Hariharan, P.C.¹ Pople, J.A.²

45
- 84961985847
- (1998) J. Phys. Chem. A , vol.102 , pp. 1995-2001
- Barone, V.¹ Cossi, M.²

46
- 84962428785
- (1998) J. Comput. Chem. , vol.19 , pp. 404-417
- Barone, B.¹ Cossi, M.² Tomasi, J.³

47
- 0011083273
- (1996) J. Phys. Chem. , vol.100 , pp. 16502-16513
- Scott, A.P.¹ Radom, L.²

48
- 84988098098
- (1987) J. Comput. Chem. , vol.8 , pp. 894-905
- Chirlian, L.E.¹ Francl, M.M.²

49
- 84986513567
- (1990) J. Comput. Chem. , vol.11 , pp. 361-373
- Breneman, C.M.¹ Wiberg, K.B.²

50
- 0026029973
- (1991) Tetrahedron , vol.47 , pp. 1707-1726
- Davies, A.G.¹ Schiesser, C.H.²

51
- 0030695183
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 9852-9855
- Chen, J.S.¹ Houk, K.N.² Foote, C.S.³

52
- 0033579583
- (1999) Tetrahedron Lett. , vol.40 , pp. 8939-8943
- Singleton, D.A.¹ Hang, C.²

53
- 0003942864
- John Wiley and Sons: New York
- (1994) Stereochemistry of Organic Compounds , pp. 615-620
- Eliel, E.L.¹ Wilen, S.H.² Mander, L.N.³

54
- 0006599397
- The energy of transition state 12d converged to -327.0653 au

55
- 0006524625
- The energy of transition state 12g converged to -327.0614 au

56
- 0006524626
- The energy intermediate 12h converged to -327.0643 au

57
- 0006560787
- The energy of transition state 14e converged to -366.3665 au

58
- 33947468884
- (1957) J. Am. Chem. Soc. , vol.79 , pp. 1920-1923
- Zimmerman, H.E.¹ Traxler, M.D.²

59
- 0001346069
- (1990) J. Org. Chem. , vol.55 , pp. 481-493
- Li, Y.¹ Paddon-Row, M.N.² Houk, K.N.³

60
- 0003942864
- John Wiley and Sons: New York
- (1994) Stereochemistry of Organic Compounds , pp. 876-891
- Eliel, E.L.¹ Wilen, S.H.² Mander, L.N.³

61
- 33845281063
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 908-910
- Wu, Y.-D.¹ Houk, K.N.²

62
- 0003942864
- John Wiley and Sons: New York
- (1994) Stereochemistry of Organic Compounds , pp. 773-777
- Eliel, E.L.¹ Wilen, S.H.² Mander, L.N.³

63
- 0345460369
- (1963) J. Org. Chem. , vol.28 , pp. 31-34
- House, H.O.¹ Ramusson, G.H.²

64
- 0000254344
- (1972) Tetrahedron , vol.28 , pp. 1191-1201
- Allinger, N.L.¹ Tribble, M.T.²

65
- 0006614369
- (1970) Acta Chem. Scand. , vol.24 , pp. 2453-2458
- Sellers, P.¹

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.