Optical resolution of racemic norbornene aldehydes: Kinetically controlled intramolecular haloetherification of ene acetals

Tetrahedron Letters

Volumn 41, Issue 11, 2000, Pages 1829-1832

  Fujioka, Hiromichi ^a   Kotoku, Naoyuki ^a   Nagatomi, Yasushi ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Ene acetal; Hydrobenzoin; Intramolecular haloetherification; Kinetic control; Norbornene aldehyde; Optical resolution

Indexed keywords

ALDEHYDE; BENZOIC ACID DERIVATIVE; NORBORNENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; OPTICAL ROTATION; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0034635860     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00039-3     Document Type: Article

References (8)

1. Fujioka, H.; Nagatomi, Y.; Kitagawa, H.; Kita, Y. J. Am. Chem. Soc. 1997, 119, 12 016-12 017; Fujioka, H.; Nagatomi, Y.; Kotoku, N.; Kitagawa, H.; Kita, Y. Tetrahedron Lett. 1998, 39, 7309-7312.
2. Fujioka, H.; Nagatomi, Y.; Kitagawa, H.; Kita, Y. J. Am. Chem. Soc. 1997, 119, 12 016-12 017; Fujioka, H.; Nagatomi, Y.; Kotoku, N.; Kitagawa, H.; Kita, Y. Tetrahedron Lett. 1998, 39, 7309-7312.
3. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238-1256.
4. Poll, T.; Hady, A. F. A.; Karge, R.; Linz, G.; Weetman, J.; Helmchen, G. Tetrahedron Lett. 1989, 30, 5595-5598; Takasu, M.; Yamamoto, H. Synlett 1990, 194-196; Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920-6930, and references cited therein.
5. Poll, T.; Hady, A. F. A.; Karge, R.; Linz, G.; Weetman, J.; Helmchen, G. Tetrahedron Lett. 1989, 30, 5595-5598; Takasu, M.; Yamamoto, H. Synlett 1990, 194-196; Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920-6930, and references cited therein.
6. Poll, T.; Hady, A. F. A.; Karge, R.; Linz, G.; Weetman, J.; Helmchen, G. Tetrahedron Lett. 1989, 30, 5595-5598; Takasu, M.; Yamamoto, H. Synlett 1990, 194-196; Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920-6930, and references cited therein.
7. 3 was added to the mixture. Extraction with EtOAc, the usual workup and purification by silica gel column chromatography (hexane:EtOAc) afforded 3a and 2′a.
8. 2. The mixture was stirred at around 80°C. After completion of the reaction (TLC check), the mixture was diluted with ether and filtered through a Celite pad. The filtrate was evaporated in vacuo and purified by silica gel column chromatography (hexane:EtOAc) to afford (2S)-1c and 4.