Hetero diels-alder reaction catalyzed by new axially dissymmetric ligands with fluorinated chiral centers

Heterocycles

Volumn 59, Issue 2, 2003, Pages 501-504

  Omote, Masaaki ^a   Hasegawa, Tomokuni ^a   Sato, Kazuyuki ^a   Ando, Akira ^a   Kumadaki, Itsumaro ^a  

^a SETSUNAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; ALUMINUM DERIVATIVE; BENZALDEHYDE; BIPHENYL DERIVATIVE; BIS(2,2,2 TRIFLUOROHYDROXYETHYL)BIPHENYL; LEWIS ACID; LIGAND; METAL COMPLEX; PERFLUORO COMPOUND; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; DIASTEREOISOMER; DIELS ALDER REACTION; ENANTIOMER; ENANTIOSELECTIVITY; FLUORINATION; SYNTHESIS;

EID: 0037346082     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-02-s75     Document Type: Article

References (6)

1. M. Omote, A. Kominato, M. Sugawara, K. Sato, A. Ando, and I. Kumadaki, Tetrahedron Letters, 1999, 40, 5583.
2. M. Mori and T. Nakai, Tetrahedron Letters, 1997, 38, 6233.
3. Enantiomeric excess of the product was determined using chiral capillary column (GAMMA DEX™ 225 Capillary Column, 30m × 0.25mm, SUPELCO Inc)
4. K. Maruoka, T. Itoh, T. Shirasaka, and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 310.
5. 4 the stereochemistry of the major isomer was assigned as (R). Enantiomeric excess of the product was determined by chiral HPLC column (CHIRALCEL OD, DAICEL LTD, eluent: ethanol:n-hexane = 1:9)
6. 3): - 82.78 (6 F, s), - 122.50 (2 F, dd, J = 275, 7.6 Hz), -127.87 (2 F, ddd, J = 275, 17.6, 2.3 Hz).