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Volumn , Issue 6, 2007, Pages 986-988

Enantioselective catalysis of intramolecular Morita-Baylis-Hillman and related reactions by chiral rhenium-containing phosphines of the formula (η5-C5H5)Re(NO)(PPh3)(CH 2PAr2)

Author keywords

Cyclization; Enantioselective catalysis; Morita Baylis Hillman; Organocatalysis; Phosphine; Rauhut Currier

Indexed keywords

CHLOROBENZENE; PHOSPHINE DERIVATIVE; RHENIUM;

EID: 34247156603     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-973859     Document Type: Article
Times cited : (66)

References (34)
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    • Lead references to two large families within this extensive literature: (a) Grabulosa, A.; Granell, J.; Muller, G. Coord. Chem. Rev. 2007, 251, 25.
    • Lead references to two large families within this extensive literature: (a) Grabulosa, A.; Granell, J.; Muller, G. Coord. Chem. Rev. 2007, 251, 25.
  • 5
    • 34247131074 scopus 로고    scopus 로고
    • Angew. Chem. 2006, 118, 7836.
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    • (1999) Chem , vol.111 , pp. 1248
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  • 23
    • 34247176050 scopus 로고    scopus 로고
    • General Procedures (a) Racemic catalysts: A Schlenk flask was charged with the educt (typically 0.060-0.080 g, Then C6H 5Cl or C6H6 solutions that were 0.0125 M in ClCH2CH2Cl (reference for 1H NMR integration) were added to give 0.100 M educt solutions. These were equilibrated to 20°C using a cryostat. Solutions of C6H5Cl or C 6H6 that were 0.0100 M in catalyst and 0.0125 M in ClCH2CH2Cl were cooled to 0°C. Equal corresponding to 10 mol% loading, were added dropwise over ca. 5 min to the educt solutions. An aliquot (0.6 mL) was transferred to an NMR tube, and 1H NMR spectra were periodically recorded. When the reaction was complete (or no further reaction took place, 5 of hexane were added with stirring. The mixture was filtered through a short plug of silica gel removing catalyst, and the plug was
    • 5Cl were further purified by silica gel column chromatography, except in the case of 5a.
  • 24
    • 34247160650 scopus 로고    scopus 로고
    • Enantiopure catalysts: The preceding reactions were repeated on 0.0010-0.0020 g scales. The products were analyzed by HPLC using Chiralcel OD, Chiralpak AD-H or Chiralpak AS-H columns.
    • (b) Enantiopure catalysts: The preceding reactions were repeated on 0.0010-0.0020 g scales. The products were analyzed by HPLC using Chiralcel OD, Chiralpak AD-H or Chiralpak AS-H columns.
  • 25
    • 34247105145 scopus 로고    scopus 로고
    • All products were characterized by NMR (1H, 13C) and IR spectroscopy, and these data are available from the authors upon request; 3a,d and 5a have been reported previously.11a,15,16 Typical data (3b, 1H NMR (400 MHz, CDCl3, δ, 1.39 [d, CH3)2CH, 3J(H,H, 7.2 Hz, 6 H, 1.82-1.91 (m, C=CHCHH′, 1 H, 2.27-246 (2 m, C=CHCHH′, CHH′CHOH, 2 H) 2.62-2.73 (m, CHH′CHOH, 1 H, 2.78 (br s, CHOH, 1 H, 3.74 [sep, 3J(H,H, 7.2 Hz, CH3)2CH, 1 H, 5.13-5.16 (m, CHOH, 1 H, 6.89 [dd, 3J(H,H, 2.8, 2.8 Hz, C=CHCHH′, 1 H] ppm. 13C{1H} NMR (101 MHz, CDCl3, δ, 23.0 [s, CH3) 2CH, 30.9 (s, C=CHCH2, 31.8 s, CH 2CHOH, 34.3 [s, CH
    • -1.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.