Enantioselective aldol-type reaction using diketene

Synthetic Communications

Volumn 34, Issue 24, 2004, Pages 4487-4492

  Kawase, Takahiro ^a   Takizawa, Shinobu ^a   Jayaprakash, Doss ^a   Sasai, Hiroaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Aldol type reaction; Diketene; Enantioselective; Titanium BINOL complexes

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; ESTER DERIVATIVE; ISOPROPYL 5 HYDROXY 7 PHENYL 3 OXO 6 HEPTENOATE; KETENE DERIVATIVE; SCHIFF BASE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE;

EID: 11244327818     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200043192     Document Type: Article

References (17)

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12. For reviews on binaphthol and binaphthol-titanium complexes, see: Pu, L. Chem. Rev. 1998, 98, 2405.
13. 3, the reaction proceeded smoothly but enantiomeric excess was very low.
14. 4 (5% ee).
15. Effect of reaction temperature: -20°C (37%, 23% ee, 96h), -40°C (23%, 9% ee, 96 h), reflux (trace, 24 h). Result of other solvents: THF (30%, 23% ee, 24 h), ether (trace, 24 h), MeCN (trace, 24 h).
16. Results of reactions using other aldehydes under identical condition; 4-methoxycinnnamaldehyde (31%, 83% ee), 2-methoxycinnamaldehyde (34%, 73% ee), cyclohexanecarboxaldehyde (18%, 31% ee).
17. Benson, S.C.; Cai, P.; Colon, M.; Haiza, M.A.; Tokles, M.; Snyder, J.K. J. Org. Chem. 1988, 53, 5335.