SCOPUS 정보 검색 플랫폼

Volumn 34, Issue 44, 1993, Pages 7027-7030

Bis(imine)-copper(II) complexes as chiral lewis acid catalysts for the Diels-Alder reaction

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLINE DERIVATIVE; THIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; METHODOLOGY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0027426951 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)61588-5 Document Type: Article

Times cited : (119)

References (15)

1
- 85008090337
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 726-728
- Evans¹ Woerpel² Hinman³ Faul⁴

3
- 0342740235
- For our results employing Bis(oxazoline) ligands in the Diels-Alder reation, see
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 6460-6461
- Evans¹ Miller² Lectka³

4
- 0007448978
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 5326-5327
- Li¹ Conser² Jacobsen³

5
- 84914369698
- Our studies on olefin aziridination provide evidence that the the active catalyst in these reactions is the Cu(II)-(ligand) complex, Ref 3.

6
- 84914369697
- The requisite diimine ligands can be synthesized by refluxing 1 equiv of enantiomerically pure diamine with 2 equiv of aldehyde in benzene with azeotropic removal of water, followed by concentration and recrystallization of the resulting solid from varying proportions of ethyl acetate:hexane.

7
- 84914369696
- 2) at room temperature under nitrogen. Vigorous stirring was continued for 5h, forming a homogeneous but slightly cloudy purple-blue solution of the ligand complex. Dienophile (1 mmol) was added at −78 °C, followed by cyclopentadiene (10 mmol). The reaction pot was maintained at the isotherm for the specified time, diluted with ether, and filtered through a small plug (1 cm × 2 cm) of silica gel. The plug was washed repeatedly with ether (3 × 10 mL) to ensure elution of the product. Analysis of the crude reaction mixture was performed by HPLC on a Daicel Chiralcel@ column. Chromatography on silica yielded the pure Diels-Alder adducts.

8
- 84914369695
- Competition experiments have established that the sulfur analogues 4b–4d are 20–30 times as reactive as their oxygen counterparts 2b–2d, Ref 4.

9
- 33845280186
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 1238-1256
- Evans¹ Chapman² Bisaha³

10
- 33745424821
- For the sake of the ensuing analysis it is assumed without corroborating evidence, that both triflate ligands are dissociated from the metal center. For an X-ray structure of the related 1c-Cu(I)OTf complex see:
- (1992) Angew. Chem. Int. Ed. Eng. , vol.31 , pp. 430-432
- Evans¹ Woerpel² Scott³

12
- 0000684712
- For a discussion on the coordination chemistry of Cu(II), see, G. Wilkinson, R.D. Gillard, J.A. McClevarty, Pergamon Press, Oxford
- (1989) Comprehensive Corrdination Chemistry , vol.5 , pp. 533-750
- Hathaway¹

13
- 84914369693
- Initially the double stereodifferentiating reactions were explored with chiral oxazolidinone derived imides. However the low diastereoselectivity of the process complicated the analysis. The achiral oxazolidinethione 6c affords cycloadducts with improved diastereoselectivity relative to the oxo-case.

14
- 33845374428
- For examples of documented non-linear effects in asymmetric catalysis, see
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 2353-2357
- Puchot¹ Samuel² Dunach³ Zhao⁴ Agami⁵ Kagan⁶

15
- 33748247006
- (1991) Angew. Chem. Int. Ed. Engl. , vol.30 , pp. 49-69
- Noyori¹ Kitamura²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.