SCOPUS 정보 검색 플랫폼

Volumn 12, Issue 36, 2014, Pages 7083-7091

Effect of conformational rigidity on the stereoselectivity of nucleophilic additions to five-membered ring bicyclic oxocarbenium ion intermediates

(3) Lavinda, Olga a Tran, Vi Tuong a Woerpel, K A a

a NEW YORK UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; RIGIDITY; STEREOSELECTIVITY; SUBSTITUTION REACTIONS;

COMPUTATIONAL MODEL; CONFORMATIONAL RIGIDITY; DIASTEREO-SELECTIVITY; FIVE-MEMBERED RINGS; NUCLEOPHILIC ADDITIONS; NUCLEOPHILIC SUBSTITUTION REACTIONS; TRANSITION STATE; UNCONSTRAINED SYSTEMS;

IONS;

ACETAL DERIVATIVE; ALLYLTRIMETHYLSILANE; FURAN DERIVATIVE; FUSED HETEROCYCLIC RINGS; TRIMETHYLSILYL DERIVATIVE;

CHEMISTRY; CONFORMATION; ELECTRON TRANSPORT; STEREOISOMERISM; SYNTHESIS;

ACETALS; BICYCLO COMPOUNDS, HETEROCYCLIC; ELECTRON TRANSPORT; FURANS; MOLECULAR CONFORMATION; STEREOISOMERISM; TRIMETHYLSILYL COMPOUNDS;

EID: 84961983862 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c4ob01251h Document Type: Article

Times cited : (22)

References (55)

1
- 84874600003
- L. Li X. Ye Y. Wu L. Gao Z. Song Z. Yin Y. Xu Org. Lett. 2013 15 1068
- (2013) Org. Lett. , vol.15 , pp. 1068
- Li, L.¹ Ye, X.² Wu, Y.³ Gao, L.⁴ Song, Z.⁵ Yin, Z.⁶ Xu, Y.⁷

2
- 83055179164
- K. Kong Z. Moussa C. Lee D. Romo J. Am. Chem. Soc. 2011 133 19844
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 19844
- Kong, K.¹ Moussa, Z.² Lee, C.³ Romo, D.⁴

3
- 84859034017
- M. K. Gurjar G. S. Yellol D. K. Mohapatra Eur. J. Org. Chem. 2012 1753
- (2012) Eur. J. Org. Chem. , pp. 1753
- Gurjar, M.K.¹ Yellol, G.S.² Mohapatra, D.K.³

4
- 0028104844
- D. J. O'Leary Y. Kishi J. Org. Chem. 1994 59 6629
- (1994) J. Org. Chem. , vol.59 , pp. 6629
- O'Leary, D.J.¹ Kishi, Y.²

5
- 0037193089
- F. Goursaud F. Peyrane A. Veyrières Tetrahedron 2002 58 3629
- (2002) Tetrahedron , vol.58 , pp. 3629
- Goursaud, F.¹ Peyrane, F.² Veyrières, A.³

6
- 0041765008
- K. Haraguchi S. Takeda H. Tanaka Org. Lett. 2003 5 1399
- (2003) Org. Lett. , vol.5 , pp. 1399
- Haraguchi, K.¹ Takeda, S.² Tanaka, H.³

7
- 84922685567
- A. Imamura T. Lowary Trends Glycosci. Glycotechnol. 2011 23 134
- (2011) Trends Glycosci. Glycotechnol. , vol.23 , pp. 134
- Imamura, A.¹ Lowary, T.²

8
- 0001378935
- H. Vorbrüggen B. Bennua Tetrahedron Lett. 1978 1339
- (1978) Tetrahedron Lett. , pp. 1339
- Vorbrüggen, H.¹ Bennua, B.²

9
- 0037714410
- H. Vorbrüggen C. Ruh-Polenz Org. React. 2000 55 1
- (2000) Org. React. , vol.55 , pp. 1
- Vorbrüggen, H.¹ Ruh-Polenz, C.²

10
- 3142736550
- Q. Wu C. Simons Synthesis 2004 1533
- (2004) Synthesis , pp. 1533
- Wu, Q.¹ Simons, C.²

11
- 0033616106
- C. H. Larsen B. H. Ridgway J. T. Shaw K. A. Woerpel J. Am. Chem. Soc. 1999 121 12208
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 12208
- Larsen, C.H.¹ Ridgway, B.H.² Shaw, J.T.³ Woerpel, K.A.⁴

12
- 0242414726
- D. M. Smith M. B. Tran K. A. Woerpel J. Am. Chem. Soc. 2003 125 14149
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 14149
- Smith, D.M.¹ Tran, M.B.² Woerpel, K.A.³

13
- 0006950022
- A. Schmitt H.-U. Reissig Eur. J. Org. Chem. 2001 1169
- (2001) Eur. J. Org. Chem. , pp. 1169
- Schmitt, A.¹ Reissig, H.-U.²

14
- 0033676341
- A. Schmitt H.-U. Reissig Eur. J. Org. Chem. 2000 3893
- (2000) Eur. J. Org. Chem. , pp. 3893
- Schmitt, A.¹ Reissig, H.-U.²

15
- 0007379940
- A. Schmitt H.-U. Reissig Chem. Ber. 1995 128 871
- (1995) Chem. Ber. , vol.128 , pp. 871
- Schmitt, A.¹ Reissig, H.-U.²

16
- 85034939664
- A. Schmitt H.-U. Reissig Synlett 1990 40
- (1990) Synlett , pp. 40
- Schmitt, A.¹ Reissig, H.-U.²

17
- 84877889174
- Z. Zhang Y. Ding J. Xu Y. Chen C. J. Forsyth Org. Lett. 2013 15 2338
- (2013) Org. Lett. , vol.15 , pp. 2338
- Zhang, Z.¹ Ding, Y.² Xu, J.³ Chen, Y.⁴ Forsyth, C.J.⁵

18
- 84879402854
- E. R. van Rijssel T. P. M. Goumans G. Lodder H. S. Overkleeft G. A. van der Marel J. D. C. Codée Org. Lett. 2013 15 3026
- (2013) Org. Lett. , vol.15 , pp. 3026
- Van Rijssel, E.R.¹ Goumans, T.P.M.² Lodder, G.³ Overkleeft, H.S.⁴ Van Der Marel, G.A.⁵ Codée, J.D.C.⁶

19
- 84880181865
- J. Miguélez A. Boto R. Marín M. Díaz Eur. J. Med. Chem. 2013 66 540
- (2013) Eur. J. Med. Chem. , vol.66 , pp. 540
- Miguélez, J.¹ Boto, A.² Marín, R.³ Díaz, M.⁴

20
- 84877127509
- H. A. V. Kistemaker G. J. van der Heden van Noort H. S. Overkleeft G. A. van der Marel D. V. Filippov Org. Lett. 2013 15 2306
- (2013) Org. Lett. , vol.15 , pp. 2306
- Kistemaker, H.A.V.¹ Van Der Heden Van Noort, G.J.² Overkleeft, H.S.³ Van Der Marel, G.A.⁴ Filippov, D.V.⁵

21
- 84867725244
- G. Mata N. W. Luedtke J. Org. Chem. 2012 77 9006
- (2012) J. Org. Chem. , vol.77 , pp. 9006
- Mata, G.¹ Luedtke, N.W.²

22
- 84884828979
- M. Moumé-Pymbock T. Furukawa S. Mondal D. Crich J. Am. Chem. Soc. 2013 135 14249
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 14249
- Moumé-Pymbock, M.¹ Furukawa, T.² Mondal, S.³ Crich, D.⁴

23
- 84875175541
- The numbering used in this paper considers the carbocationic carbon as C-1
- T. G. Frihed M. T. C. Walvoort J. D. C. Codée G. A. van der Marel M. Bols C. M. Pedersen J. Org. Chem. 2013 78 2191
- (2013) J. Org. Chem. , vol.78 , pp. 2191
- Frihed, T.G.¹ Walvoort, M.T.C.² Codée, J.D.C.³ Van Der Marel, G.A.⁴ Bols, M.⁵ Pedersen, C.M.⁶

24
- 84880003009
- V. T. Tran K. A. Woerpel J. Org. Chem. 2013 78 6609
- (2013) J. Org. Chem. , vol.78 , pp. 6609
- Tran, V.T.¹ Woerpel, K.A.²

25
- 33947281216
- R. A. Dueñes J. P. Morken Synlett 2007 587
- (2007) Synlett , pp. 587
- Dueñes, R.A.¹ Morken, J.P.²

26
- 23744510729
- C. H. Larsen B. H. Ridgway J. T. Shaw D. M. Smith K. A. Woerpel J. Am. Chem. Soc. 2005 127 10879
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 10879
- Larsen, C.H.¹ Ridgway, B.H.² Shaw, J.T.³ Smith, D.M.⁴ Woerpel, K.A.⁵

27
- 77951135761
- J. S. Rhoad B. A. Cagg P. W. Carver J. Phys. Chem. A 2010 114 5180
- (2010) J. Phys. Chem. A , vol.114 , pp. 5180
- Rhoad, J.S.¹ Cagg, B.A.² Carver, P.W.³

28
- 2442707517
- S. Obika T. Osaki M. Sekiguchi R. Somjing Y. Harada T. Imanishi Tetrahedron Lett. 2004 45 4801
- (2004) Tetrahedron Lett. , vol.45 , pp. 4801
- Obika, S.¹ Osaki, T.² Sekiguchi, M.³ Somjing, R.⁴ Harada, Y.⁵ Imanishi, T.⁶

29
- 0001177017
- E. J. Corey P. B. Hopkins Tetrahedron Lett. 1982 23 4871
- (1982) Tetrahedron Lett. , vol.23 , pp. 4871
- Corey, E.J.¹ Hopkins, P.B.²

30
- 84876585427
- S. Nicolai R. Sedigh-Zadeh J. Waser J. Org. Chem. 2013 78 3783
- (2013) J. Org. Chem. , vol.78 , pp. 3783
- Nicolai, S.¹ Sedigh-Zadeh, R.² Waser, J.³

31
- 0032578717
- F. Simart Y. Brunel S. Robin G. Rousseau Tetrahedron 1998 54 13557
- (1998) Tetrahedron , vol.54 , pp. 13557
- Simart, F.¹ Brunel, Y.² Robin, S.³ Rousseau, G.⁴

32
- 0000444566
- G. Hagen H. Mayr J. Am. Chem. Soc. 1991 113 4954
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 4954
- Hagen, G.¹ Mayr, H.²

33
- 16244420717
- E. A. Colby K. C. O'Brien T. F. Jamison J. Am. Chem. Soc. 2005 127 4297
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 4297
- Colby, E.A.¹ O'Brien, K.C.² Jamison, T.F.³

34
- 44949194872
- S. G. Smith R. S. Paton J. W. Burton J. M. Goodman J. Org. Chem. 2008 73 4053
- (2008) J. Org. Chem. , vol.73 , pp. 4053
- Smith, S.G.¹ Paton, R.S.² Burton, J.W.³ Goodman, J.M.⁴

35
- 84895468680
- P. H. Willoughby M. J. Jansma T. R. Hoye Nat. Protocols 2014 9 643
- (2014) Nat. Protocols , vol.9 , pp. 643
- Willoughby, P.H.¹ Jansma, M.J.² Hoye, T.R.³

36
- 84856301655
- M. W. Lodewyk M. R. Siebert D. J. Tantillo Chem. Rev. 2012 112 1839
- (2012) Chem. Rev. , vol.112 , pp. 1839
- Lodewyk, M.W.¹ Siebert, M.R.² Tantillo, D.J.³

37
- 33746115758
- S. D. Rychnovsky Org. Lett. 2006 8 2895
- (2006) Org. Lett. , vol.8 , pp. 2895
- Rychnovsky, S.D.¹

38
- 33749619327
- E. L. Eliel Acc. Chem. Res. 1970 3 1
- (1970) Acc. Chem. Res. , vol.3 , pp. 1
- Eliel, E.L.¹

39
- 0001048152
- J. B. Lambert C. E. Mixan D. H. Johnson J. Am. Chem. Soc. 1973 95 4634
- (1973) J. Am. Chem. Soc. , vol.95 , pp. 4634
- Lambert, J.B.¹ Mixan, C.E.² Johnson, D.H.³

40
- 33748513467
- Low-energy conformations were identified by conformational searching using semi-empirical methods (PM3). The lowest-energy structures were optimized using PCM-B3LYP/6-31+G**. Details are provided as ESI.
- X. Zhu S. Kawatkar Y. Rao G.-J. Boons J. Am. Chem. Soc. 2006 128 11948
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 11948
- Zhu, X.¹ Kawatkar, S.² Rao, Y.³ Boons, G.-J.⁴

41
- 0012118862
- M. J. Robins J. S. Wilson L. Sawyer M. N. G. James Can. J. Chem. 1983 61 1911
- (1983) Can. J. Chem. , vol.61 , pp. 1911
- Robins, M.J.¹ Wilson, J.S.² Sawyer, L.³ James, M.N.G.⁴

42
- 84879104309
- J. Dillen Struct. Chem. 2013 24 751
- (2013) Struct. Chem. , vol.24 , pp. 751
- Dillen, J.¹

43
- 37149042810
- F. Freeman J. H. Hwang E. H. Junge P. D. Parmar Z. Renz J. Trinh Int. J. Quantum Chem. 2008 108 339
- (2008) Int. J. Quantum Chem. , vol.108 , pp. 339
- Freeman, F.¹ Hwang, J.H.² Junge, E.H.³ Parmar, P.D.⁴ Renz, Z.⁵ Trinh, J.⁶

44
- 0000650282
- D. F. Bocian H. L. Strauss J. Am. Chem. Soc. 1977 99 2876
- (1977) J. Am. Chem. Soc. , vol.99 , pp. 2876
- Bocian, D.F.¹ Strauss, H.L.²

45
- 33748428923
- L. F. Tietze T. Kinzel S. Schmatz J. Am. Chem. Soc. 2006 128 11483
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 11483
- Tietze, L.F.¹ Kinzel, T.² Schmatz, S.³

46
- 0034597491
- S. K. Bur S. F. Martin Org. Lett. 2000 2 3445
- (2000) Org. Lett. , vol.2 , pp. 3445
- Bur, S.K.¹ Martin, S.F.²

47
- 43049141516
- Y. Zhao D. G. Truhlar Theor. Chem. Acc. 2007 120 215
- (2007) Theor. Chem. Acc. , vol.120 , pp. 215
- Zhao, Y.¹ Truhlar, D.G.²

48
- 33645949559
- M. M. Francl W. J. Pietro W. J. Hehre J. S. Binkley M. S. Gordon D. J. DeFrees J. A. Pople J. Chem. Phys. 1982 77 3654
- (1982) J. Chem. Phys. , vol.77 , pp. 3654
- Francl, M.M.¹ Pietro, W.J.² Hehre, W.J.³ Binkley, J.S.⁴ Gordon, M.S.⁵ Defrees, D.J.⁶ Pople, J.A.⁷

49
- 33748545144
- P. C. Hariharan J. A. Pople Theor. Chim. Acta 1973 28 213
- (1973) Theor. Chim. Acta , vol.28 , pp. 213
- Hariharan, P.C.¹ Pople, J.A.²

50
- 84946893847
- S. MiertuŠ E. Scrocco J. Tomasi Chem. Phys. 1981 55 117
- (1981) Chem. Phys. , vol.55 , pp. 117
- Miertuš, S.¹ Scrocco, E.² Tomasi, J.³

51
- 84894443889
- D. Nitsch S. M. Huber A. Pöthig A. Narayanan G. A. Olah G. K. S. Prakash T. Bach J. Am. Chem. Soc. 2014 136 2851
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 2851
- Nitsch, D.¹ Huber, S.M.² Pöthig, A.³ Narayanan, A.⁴ Olah, G.A.⁵ Prakash, G.K.S.⁶ Bach, T.⁷

52
- 84962446719
- H. A. Dabbagh M. Zamani S. Fakhraee Res. Chem. Intermed. 2012 38 1551
- (2012) Res. Chem. Intermed. , vol.38 , pp. 1551
- Dabbagh, H.A.¹ Zamani, M.² Fakhraee, S.³

53
- 15444368955
- K. Hassall S. Lobachevsky J. M. White J. Org. Chem. 2005 70 1993
- (2005) J. Org. Chem. , vol.70 , pp. 1993
- Hassall, K.¹ Lobachevsky, S.² White, J.M.³

54
- 77955700674
- D. Crich Acc. Chem. Res. 2010 43 1144
- (2010) Acc. Chem. Res. , vol.43 , pp. 1144
- Crich, D.¹

55
- 5244370033
- A. B. Pangborn M. A. Giardello R. H. Grubbs R. K. Rosen F. J. Timmers Organometallics 1996 15 1518
- (1996) Organometallics , vol.15 , pp. 1518
- Pangborn, A.B.¹ Giardello, M.A.² Grubbs, R.H.³ Rosen, R.K.⁴ Timmers, F.J.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.