Catalytic enantioselective homoaldol reactions using binol titanium(IV) fluoride catalysts

Synlett

Volumn , Issue 3, 2003, Pages 390-392

  Burke, E Diane ^a   Lim, Ngiap Kie ^a   Gleason, James L ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

Asymmetric catalysis; Homoaldol additions; Homoenolates; Titanium(IV) fluorides

Indexed keywords

1 ETHOXY 1 (TRIMETHYLSILYLOXY)CYCLOPROPANE; 2,2' BINAPHTHOL; ALDEHYDE DERIVATIVE; CYCLOPROPANE DERIVATIVE; FLUORIDE; NAPHTHOL DERIVATIVE; SILICON; TITANIUM; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL PROCEDURES; CHEMICAL REACTION; COMPARATIVE STUDY; ELIMINATION REACTION; ENANTIOSELECTIVITY; ENZYME SUBSTRATE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037289455     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37122     Document Type: Article

References (10)

1. For reviews on the homoaldol reaction, see: (a) Crimmins, M. T.; Nantermet, P. G. Org. Prep. Proc. 1993, 25, 43. (b) Kuwajima, I.; Nakamura, E. In Comprehensive Organic Synthesis, Vol 2; Trost, B. M.; Fleming, I., Eds.; Pergammon: Oxford., 1991, 441.
2. For reviews on the homoaldol reaction, see: (a) Crimmins, M. T.; Nantermet, P. G. Org. Prep. Proc. 1993, 25, 43. (b) Kuwajima, I.; Nakamura, E. In Comprehensive Organic Synthesis, Vol 2; Trost, B. M.; Fleming, I., Eds.; Pergammon: Oxford., 1991, 441.
3. Weber, B.; Seebach, D. Tetrahedron 1994, 50, 7473.
4. Martins, E. O.; Gleason, J. L. Org. Lett. 1999, 1, 1643.
5. (a) Gauthier, D. R. Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
6. (b) Bode, J. W.; Gauthier, D. R. Jr.; Carreira, E. M. Chem. Commun. 2001, 24, 2560.
7. (b) Pagenkopf, B. L.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 9593.
8. The absolute stereochemistry was established as R by comparison of the optical rotation of 4 with literature values: Gutman, A. L.; Zuobi, K.; Bravdo, T. J. Org. Chem. 1990, 55, 3546.
9. 8-Binol and TADDOL did not afford any increase in enantioselectivity.
10. 2: C, 74.06; H, 6.21. Found: C, 73.73; H, 6.02.