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Volumn , Issue 10, 2008, Pages 1557-1561

Allylic substitution of meso-1,4-diacetoxycycloalkenes in water with an amphiphilic resin-supported chiral palladium complex

Author keywords

allylpalladium; Aqueous media; Asymmetric catalysis; Palladium catalyst; Polymer support

Indexed keywords

CYCLOALKENE; MACROGOL; MESO 1,4 DIACETOXYCYCLOHEXENE; MESO 1,4 DIACETOXYCYCLOPENTENE; PALLADIUM COMPLEX;

EID: 46649117695     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078422     Document Type: Article
Times cited : (22)

References (54)
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    • 2 (purchased from Rapp Polymere) was used as the polymer support.
    • 2 (purchased from Rapp Polymere) was used as the polymer support.
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    • 3.
    • 3.
  • 51
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    • The absolute configuration of 4 was determined by chemical correlation with (1R, 4S)-cis-1-acetoxy-4-[bis(methoxy-carbonyl) methyl]-2-cyclopentene (see ref. 8a).
    • The absolute configuration of 4 was determined by chemical correlation with (1R, 4S)-cis-1-acetoxy-4-[bis(methoxy-carbonyl) methyl]-2-cyclopentene (see ref. 8a).
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    • The absolute configuration of 6a was determined to be 1R, 4S by measurement of the specific rotation (see, ref. 12). The configurations of 6b-g were tentatively assigned on the basis of the mechanistic similarity of the asymmetric induction, as depicted in Table 1.
    • The absolute configuration of 6a was determined to be 1R, 4S by measurement of the specific rotation (see, ref. 12). The configurations of 6b-g were tentatively assigned on the basis of the mechanistic similarity of the asymmetric induction, as depicted in Table 1.
  • 54
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    • Palladium-Catalyzed Asymmetric Desymmetrization of iweso-Cycloalkene-1,4-diacetate: Reaction conditions and results are shown in Table 1. A typical procedure is given for the reaction with cis-1,4-diacetoxycyclopentene (meso-2) and phenol (a) in H 2O (entry 3, To a mixture of the catalyst 1 (89 mg, 0.025 mmol) and meso-2 (92 mg, 0.5 mmol) in H2O (2.5 mL) was added phenol (48 mg, 0.5 mmol, and the mixture was shaken at 0 °C for 18 h. The reaction mixture was filtered and the recovered resin beads were rinsed with EtOAc (3 x, The combined filtrate was dried over anhyd Na2SO4. The solvent was evaporated and the residue was chromatographed on silica gel (hexane-EtOAc, 10:1) to give l-acetoxy-4-phenoxycyclopentene (6a; 70 mg, 64% yield) and 1,4-diphenoxycyclopentene (8; 18 mg, The enantiomeric excess was determined to be 99% ee by GC analysis using a chiral stationary phase capillary column Cyclod
    • 3): δ = 170.84, 153.65, 134.65, 134.46, 130.57, 127.66, 123.71, 121.94, 115.26, 81.33, 76.61, 38.02,21.11. IR (ATR)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.