SCOPUS 정보 검색 플랫폼

Volumn 46, Issue 3, 2010, Pages 445-447

Expanded scope for the iridium-catalyzed asymmetric isomerization of primary allylic alcohols using readily accessible second-generation catalysts

(2) Mantilli, Luca a Mazet, Clément a

a UNIVERSITY OF GENEVA (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; IRIDIUM; SERINE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TEMPERATURE DEPENDENCE;

EID: 75649144343 PISSN: 13597345 EISSN: None Source Type: Journal
DOI: 10.1039/b920342g Document Type: Article

Times cited : (62)

References (17)

1
- 0034697497
- H. U. Blaser and E. Schmidt, Wiley-VCH, Weinheim
- Asymmetric catalysis on industrial scale: challenges, approaches, and solutions, ed., H. U. Blaser, and, E. Schmidt, Wiley-VCH, Weinheim, 2003
- (2003) Asymmetric Catalysis on Industrial Scale: Challenges, Approaches, and Solutions, Ed.

2
- 70349911865
- For recent reviews, see
- L. Mantilli D. Gérard S. Torche C. Besnard C. Mazet Angew. Chem., Int. Ed. 2009 48 5143
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 5143
- Mantilli, L.¹ Gérard, D.² Torche, S.³ Besnard, C.⁴ Mazet, C.⁵

3
- 0036569365
- R. C. Van der Drift E. Bouwman E. Drent J. Organomet. Chem. 2002 650 1
- (2002) J. Organomet. Chem. , vol.650 , pp. 1
- Van Der Drift, R.C.¹ Bouwman, E.² Drent, E.³

4
- 0037239704
- R. Uma C. Crévisy R. Grée Chem. Rev. 2003 103 27
- (2003) Chem. Rev. , vol.103 , pp. 27
- Uma, R.¹ Crévisy, C.² Grée, R.³

5
- 44349092408
- For other examples of enantioselective isomerization of primary allylic alcohols, see
- V. Cadierno P. Crochet J. Gimeno Synlett 2008 8 1105
- (2008) Synlett , vol.8 , pp. 1105
- Cadierno, V.¹ Crochet, P.² Gimeno, J.³

6
- 0000156672
- C. Botteghi G. Giacomelli Gazz. Chim. Ital. 1976 106 1131
- (1976) Gazz. Chim. Ital. , vol.106 , pp. 1131
- Botteghi, C.¹ Giacomelli, G.²

7
- 0034638371
- K. Tanaka S. Qiao M. Tobisu M. M.-C. Lo G. C. Fu J. Am. Chem. Soc. 2000 122 9870
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 9870
- Tanaka, K.¹ Qiao, S.² Tobisu, M.³ Lo, M.M.-C.⁴ Fu, G.C.⁵

8
- 0035977219
- K. Tanaka G. C. Fu J. Org. Chem. 2001 66 8177
- (2001) J. Org. Chem. , vol.66 , pp. 8177
- Tanaka, K.¹ Fu, G.C.²

9
- 0035124304
- C. Chapuis M. Barthe J.-Y. de Saint Laumer Helv. Chim. Acta 2001 84 230
- (2001) Helv. Chim. Acta , vol.84 , pp. 230
- Chapuis, C.¹ Barthe, M.² De Saint Laumer, J.-Y.³

10
- 33744972845
- F. Boeda P. Mosset C. Crévisy Tetrahedron Lett. 2006 47 5021
- (2006) Tetrahedron Lett. , vol.47 , pp. 5021
- Boeda, F.¹ Mosset, P.² Crévisy, C.³

11
- 4644240867
- A. Doppiu A. Salzer Eur. J. Inorg. Chem. 2004 2244
- (2004) Eur. J. Inorg. Chem. , pp. 2244
- Doppiu, A.¹ Salzer, A.²

12
- 50849104806
- S. Bovo A. Scrivanti M. Bertoldini V. Beghetto U. Matteoli Synthesis 2008 16 2547
- (2008) Synthesis , vol.16 , pp. 2547
- Bovo, S.¹ Scrivanti, A.² Bertoldini, M.³ Beghetto, V.⁴ Matteoli, U.⁵

13
- 18244394041
- M. Ito S. Kitahara T. Ikariya J. Am. Chem. Soc. 2005 127 6172
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 6172
- Ito, M.¹ Kitahara, S.² Ikariya, T.³

14
- 0032538022
- A. M. Porte J. Reibenspies K. Burgess J. Am. Chem. Soc. 1998 120 9180
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 9180
- Porte, A.M.¹ Reibenspies, J.² Burgess, K.³

15
- 0032540966
- Prices for each enantiomer of tert-leucine and serine in US $ per mol were calculated using the largest amount available from Bachem AG (September 2009)
- K. Burgess A. M. Porte Tetrahedron: Asymmetry 1998 9 2465
- (1998) Tetrahedron: Asymmetry , vol.9 , pp. 2465
- Burgess, K.¹ Porte, A.M.²

16
- 0036964808
- D. B. G. Williams H. Lombard M. van Niekerk P. P. Coetzee C. W. Holzapfel Phosphorus, Sulfur Silicon Relat. Elem. 2002 177 2799
- (2002) Phosphorus, Sulfur Silicon Relat. Elem. , vol.177 , pp. 2799
- Williams, D.B.G.¹ Lombard, H.² Van Niekerk, M.³ Coetzee, P.P.⁴ Holzapfel, C.W.⁵

17
- 0032476793
- For consistency, all reactions in Fig. 2 have been run for 22 h. Some isomerization reactions may require shorter reaction time to reach the indicated yields. Nevertheless, if the isomerizations are run for longer period of time, the yields are not improved. For allylic alcohols 3a-e, reactions have been scaled up to a 2 mmol scale using 2b without erosion of neither the yields nor the enantioselectivities Isomerization of (Z)-configured primary allylic alcohols is still problematic with these (P,N)-iridium catalysts. Low conversions and enantioselectivities along with substantial competing (E)/(Z) isomerization were obtained. See also ref. 2 and 4a
- A. Lightfoot P. Schnider A. Pfaltz Angew. Chem., Int. Ed. 1998 37 2897
- (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2897
- Lightfoot, A.¹ Schnider, P.² Pfaltz, A.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.