Baylis-Hillman Reaction

A. B. Baylis, M. E. D. Hillman, DE 2155113; eidem, US 3743669 (1972, 1973 both to Celanese).

Coupling of activated vinyl systems with aldehydes, catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO), to yield α-hydroxyalkylated or -arylated products:

Mechanistic studies: Y. Fort et al., Tetrahedron 48, 6371 (1992); E. L. M. van Rozendaal et al., ibid. 49, 6931 (1993); K. E. Price et al., J. Org. Chem. 70, 3980 (2005). Rate enhancement study: J. Augé et al., Tetrahedron Lett. 35, 7947 (1994). Use of chiral auxillary: S. E. Drewes et al., Synth. Commun. 23, 1215 (1993). Synthetic applications: idem et al., ibid. 2807; P. Perlmutter, T. D. McCarthy, Aust. J. Chem. 46, 253 (1993). Reviews: S. E. Drewes, G. H. P. Roos, Tetrahedron 44, 4653-4670 (1988); D. Basavaiah et al., Chem. Rev. 103, 811-891 (2003).