SCOPUS 정보 검색 플랫폼

Volumn 47, Issue 27, 2011, Pages 7866-7868

Access to unusual polycyclic spiro-enones from 2,2′-bis(allyloxy)-1, 1′-binaphthyls using Grubbs' catalysts: An unprecedented one-pot RCM/Claisen sequence

(6) Piedra, Estefanía a Francos, Javier a Nebra, Noel a Suárez, Francisco J a Díez, Josefina a Cadierno, Victorio a

a UNIVERSITY OF OVIEDO (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CARBENE; HYDROGEN; NAPHTHYL GROUP; POLYCYCLIC AROMATIC COMPOUND; SPIRO COMPOUND;

ARTICLE; CATALYST; CLAISEN REARRANGEMENT; ENANTIOMER; IRRADIATION; ISOMERIZATION; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 79959791871 PISSN: 13597345 EISSN: 1364548X Source Type: Journal
DOI: 10.1039/c1cc11907a Document Type: Article

Times cited : (9)

References (34)

1
- 33644922320
- R. H. Grubbs, Wiley-VCH, Weinheim
- Handbook of Metathesis, ed., R. H. Grubbs,, Wiley-VCH, Weinheim, 2003
- (2003) Handbook of Metathesis, Ed.

2
- 36049015757
- See, for example:
- A. H. Hoveyda A. R. Zhugralin Nature 2007 450 243
- (2007) Nature , vol.450 , pp. 243
- Hoveyda, A.H.¹ Zhugralin, A.R.²

3
- 3343012187
- R. H. Grubbs Tetrahedron 2004 60 7117
- (2004) Tetrahedron , vol.60 , pp. 7117
- Grubbs, R.H.¹

4
- 2942589152
- A. Deiters S. F. Martin Chem. Rev. 2004 104 2199
- (2004) Chem. Rev. , vol.104 , pp. 2199
- Deiters, A.¹ Martin, S.F.²

5
- 34047236233
- S. K. Chattopadhyay S. Karmakar T. Biswas K. C. Majumdar H. Rahaman B. Roy Tetrahedron 2007 63 3919
- (2007) Tetrahedron , vol.63 , pp. 3919
- Chattopadhyay, S.K.¹ Karmakar, S.² Biswas, T.³ Majumdar, K.C.⁴ Rahaman, H.⁵ Roy, B.⁶

6
- 36549001142
- See, for example:
- S. Kotha K. Lahiri Synlett 2007 2767
- (2007) Synlett , pp. 2767
- Kotha, S.¹ Lahiri, K.²

7
- 0034746687
- T. M. Trnka R. H. Grubbs Acc. Chem. Res. 2001 34 18
- (2001) Acc. Chem. Res. , vol.34 , pp. 18
- Trnka, T.M.¹ Grubbs, R.H.²

8
- 68949140962
- C. Samojłowicz M. Bieniek K. Grela Chem. Rev. 2009 109 3708
- (2009) Chem. Rev. , vol.109 , pp. 3708
- Samojłowicz, C.¹ Bieniek, M.² Grela, K.³

9
- 77954897138
- S. P. Nolan H. Clavier Chem. Soc. Rev. 2010 39 3305
- (2010) Chem. Soc. Rev. , vol.39 , pp. 3305
- Nolan, S.P.¹ Clavier, H.²

10
- 33745442211
- S. K. Collins A. Grandbois M. P. Vachon J. Côté Angew. Chem., Int. Ed. 2006 45 2923
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 2923
- Collins, S.K.¹ Grandbois, A.² Vachon, M.P.³ Côté, J.⁴

11
- 67650089596
- J. Côté S. K. Collins Synthesis 2009 1499
- (2009) Synthesis , pp. 1499
- Côté, J.¹ Collins, S.K.²

12
- 0036431796
- J. K. Bremmer J. A. Coates D. R. Coghlan D. M. David P. A. Keller S. G. Pyne New J. Chem. 2002 26 1549
- (2002) New J. Chem. , vol.26 , pp. 1549
- Bremmer, J.K.¹ Coates, J.A.² Coghlan, D.R.³ David, D.M.⁴ Keller, P.A.⁵ Pyne, S.G.⁶

13
- 65149096057
- A. Garas J. B. Bremmer J. Coates J. Deadman P. A. Keller S. G. Pynes D. I. Rhodes Bioorg. Med. Chem. Lett. 2009 19 3010
- (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 3010
- Garas, A.¹ Bremmer, J.B.² Coates, J.³ Deadman, J.⁴ Keller, P.A.⁵ Pynes, S.G.⁶ Rhodes, D.I.⁷

14
- 0034082045
- M. Arisawa H. Kaneko A. Nishida K. Yamaguchi M. Nakagawa Synlett 2000 841
- (2000) Synlett , pp. 841
- Arisawa, M.¹ Kaneko, H.² Nishida, A.³ Yamaguchi, K.⁴ Nakagawa, M.⁵

15
- 0036009295
- M. Arisawa H. Kaneko A. Nishida M. Nakagawa J. Chem. Soc., Perkin Trans. 1 2002 959
- (2002) J. Chem. Soc., Perkin Trans. 1 , pp. 959
- Arisawa, M.¹ Kaneko, H.² Nishida, A.³ Nakagawa, M.⁴

16
- 29144490841
- Competitive oligomerization of the substrates is commonly observed during RCM of diolefins:
- Y. A. Ibrahim E. John Tetrahedron 2006 62 1001
- (2006) Tetrahedron , vol.62 , pp. 1001
- Ibrahim, Y.A.¹ John, E.²

17
- 68949161995
- and references cited therein
- S. Monfette D. E. Fogg Chem. Rev. 2009 109 3783
- (2009) Chem. Rev. , vol.109 , pp. 3783
- Monfette, S.¹ Fogg, D.E.²

18
- 4344610661
- A. M. M. Castro Chem. Rev. 2004 104 2939
- (2004) Chem. Rev. , vol.104 , pp. 2939
- Castro, A.M.M.¹

19
- 84889465311
- M. Hiersemann and U. Nubbemeyer, Wiley-VCH, Weinheim, Structures related to A are rare:
- Claisen Rearrangement, ed., M. Hiersemann, and, U. Nubbemeyer,, Wiley-VCH, Weinheim, 2007
- (2007) Claisen Rearrangement

20
- 0001336265
- N. Kobayashi Y. Kobayashi T. Osa J. Am. Chem. Soc. 1993 115 10994
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 10994
- Kobayashi, N.¹ Kobayashi, Y.² Osa, T.³

21
- 77954747188
- See, for example:
- A. Saad F. Barrière E. Levillain N. Vanthuyne O. Jeannin M. Fourmigué Chem.-Eur. J. 2010 16 8020
- (2010) Chem.-Eur. J. , vol.16 , pp. 8020
- Saad, A.¹ Barrière, F.² Levillain, E.³ Vanthuyne, N.⁴ Jeannin, O.⁵ Fourmigué, M.⁶

22
- 77954349799
- K. Plé A. Haudrechy N. P. Probst Tetrahedron 2010 66 5030
- (2010) Tetrahedron , vol.66 , pp. 5030
- Plé, K.¹ Haudrechy, A.² Probst, N.P.³

23
- 44949226129
- N. P. Probst A. Haudrechy K. Plé J. Org. Chem. 2008 73 4338
- (2008) J. Org. Chem. , vol.73 , pp. 4338
- Probst, N.P.¹ Haudrechy, A.² Plé, K.³

24
- 38349167624
- S. Rotzoll H. Görls P. Langer Synthesis 2008 45
- (2008) Synthesis , pp. 45
- Rotzoll, S.¹ Görls, H.² Langer, P.³

25
- 33747197191
- S. K. Chattopadhyay S. P. Roy D. Ghosh G. Biswas Tetrahedron Lett. 2006 47 6895
- (2006) Tetrahedron Lett. , vol.47 , pp. 6895
- Chattopadhyay, S.K.¹ Roy, S.P.² Ghosh, D.³ Biswas, G.⁴

26
- 33750552076
- S. Kotha K. Mandal A. Tiwari S. M. Mobin Chem.-Eur. J. 2006 12 8024
- (2006) Chem.-Eur. J. , vol.12 , pp. 8024
- Kotha, S.¹ Mandal, K.² Tiwari, A.³ Mobin, S.M.⁴

27
- 33750626553
- V. Thornqvist S. Manner O. F. Wendt T. Frejd Tetrahedron 2006 62 11793
- (2006) Tetrahedron , vol.62 , pp. 11793
- Thornqvist, V.¹ Manner, S.² Wendt, O.F.³ Frejd, T.⁴

28
- 0242361236
- P. Beaulieu W. W. Ogilvie Tetrahedron Lett. 2003 44 8883
- (2003) Tetrahedron Lett. , vol.44 , pp. 8883
- Beaulieu, P.¹ Ogilvie, W.W.²

29
- 3943048796
- B. Schmidt Eur. J. Org. Chem. 2004 1865
- (2004) Eur. J. Org. Chem. , pp. 1865
- Schmidt, B.¹

30
- 68949158621
- Note also that the observed dihedral angles between the two naphthalene ring systems in each binaphthyl unit of 3a (74.59° and 88.03° for one conformer, and 69.90° and 82.20° for the other one) are only slightly higher than that observed in the structure of its acyclic precursor 1a (69.05°), which indicates that the steric strain within 3a is low:
- B. Alcaide P. Almendros A. Luna Chem. Rev. 2009 109 3817
- (2009) Chem. Rev. , vol.109 , pp. 3817
- Alcaide, B.¹ Almendros, P.² Luna, A.³

31
- 66749115534
- t in refluxing THF:
- J.-C. Ge H. Li Acta Crystallogr., Sect. E: Struct. Rep. Online 2009 65 o1179
- (2009) Acta Crystallogr., Sect. E: Struct. Rep. Online , vol.65 , pp. 1179
- Ge, J.-C.¹ Li, H.²

32
- 37049139077
- 3:
- F. De Jong M. E. Siegel D. J. Cram J. Chem. Soc., Chem. Commun. 1975 551
- (1975) J. Chem. Soc., Chem. Commun. , pp. 551
- De Jong, F.¹ Siegel, M.E.² Cram, D.J.³

33
- 0033498849
- Concerning compound C, it was generated by thermal treatment (210 °C) of 2-allyloxy-2′-hydroxy-1,1′-binaphthyl under reduced pressure:
- A. R. Ramesha K. Vishnumurthy T. N. G. Row S. Chandrasekaran Indian J. Chem., Sect. B 1999 38 1015
- (1999) Indian J. Chem., Sect. B , vol.38 , pp. 1015
- Ramesha, A.R.¹ Vishnumurthy, K.² Row, T.N.G.³ Chandrasekaran, S.⁴

34
- 0007922977
- Evolution of 3a into 2a with longer reaction times was not observed, thus allowing us to discard its participation as a reaction intermediate In all the reactions depicted in Scheme 2 formation of minor amounts of macrocyclic dimers related to 3a, as well as higher oligomers, was evidenced from the NMR spectra of the crude reaction mixtures. One of these dimers, i.e.3b, could be isolated in pure form (9%) allowing its unambiguous characterization (see ESI)
- Y. Nakamura R. Hollenstein J. Zsindely H. Schmid W. E. Oberhänsli Helv. Chim. Acta 1975 58 1949
- (1975) Helv. Chim. Acta , vol.58 , pp. 1949
- Nakamura, Y.¹ Hollenstein, R.² Zsindely, J.³ Schmid, H.⁴ Oberhänsli, W.E.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.