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Volumn , Issue 13, 2007, Pages 2057-2060

Enantioselective copper-catalyzed conjugate addition to 2- or 3-substituted cyclopent-2-en-1-ones: Construction of stereogenic quaternary carbon centers

Author keywords

Aluminum; Asymmetric catalysis; Copper; Ligands; Michael addition

Indexed keywords

ALUMINUM DERIVATIVE; COPPER; CYCLOPENT 2 EN 1 ONE; CYCLOPENTANONE DERIVATIVE; PHOSPHORAMIDOUS ACID; TRIETHYLALUMINUM; TRIMETHYLALUMINUM; UNCLASSIFIED DRUG;

EID: 34548162908     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984889     Document Type: Article
Times cited : (48)

References (30)
  • 5
    • 0036793999 scopus 로고    scopus 로고
    • For reviews on asymmetric conjugate additions, see: a
    • For reviews on asymmetric conjugate additions, see: (a) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221.
    • (2002) Eur. J. Org. Chem , pp. 3221
    • Alexakis, A.1    Benhaim, C.2
  • 20
    • 34548152735 scopus 로고    scopus 로고
    • General Procedure for the Cu-Catalyzed A.C.A. of R3Al in the Presence of Phosphoramidite Ligand A flame-dried Schlenk tube was charged with [CuOTf]2·C6H6 (2.0 mol, and L3 (8.0 mol, Then Et2O (2.5 mL) was added and the mixture was stirred at r.t. for 30 min. Afterwards, the substrate (1.0 equiv, 1.0 mmol) in Et2O (0.5 mL) was added dropwise at r.t. and the reaction mixture was stirred for further 5 min before being cooled to -30°C. Then, R3Al was introduced dropwise over 2 min. Once the addition was complete the reaction mixture was left at -30°C overnight. The reaction was hydrolyzed by the addition of MeOH at -30°C, followed by 2 N HCl (3 mL) at r.t. Subsequently, Et2O (10 mL) was added and the aqueous layer was separated and extracted further with Et2O (3 x 3 mL, The combined organic fractions were washed with brine 5 mL, dried over Na 2
    • 2O) to yield the 1,4-adduct. Gas chromatography on a chiral stationary phase indicated the ee.
  • 21
    • 34548146765 scopus 로고    scopus 로고
    • General Procedure for the Cu-Catalyzed A.C.A. of R3Al in the Presence of Diphosphite Ligand A flame-dried Schlenk tube was charged with Cu(OTf)2 (4.0 mol, and L6 (8.0 mol, Then, Et 2O (8.0 mL) was added and the mixture was stirred at r.t. for 30 min. Afterwards, the substrate (1.0 equiv, 1.0 mmol) in Et2O (0.5 mL) was added dropwise at r.t. and the reaction mixture was stirred for further 5 min before being cooled to -30°C. Then, R3Al was introduced dropwise over 2 min. Once the addition completed, the reaction mixture was left at -30°C overnight. The reaction was hydrolyzed by the addition of MeOH at -30°C, followed by aq sat. NH4Cl solution (3 mL) at r.t. Subsequently, Et2O (10 mL) was added and the aqueous layer was separated and extracted further with Et2O (3 x 3 mL, The combined organic fractions were washed with brine 5 mL, dried over anhyd Na 2SO
    • 2O) to yield the 1,4-adduct. Gas chromatography on a chiral stationary phase indicated the ee.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.