Henry Reaction (Nitroaldol Reaction)

L. Henry, Compt. Rend. 120, 1265 (1895); J. Kamlet, US 2151517 (1939).

Base-catalyzed aldol-type condensation, q.v., of nitroalkanes with aldehydes or ketones:

Application to sugars: R. Fernández et al., Carbohydr. Res. 247, 239 (1993). Reagent controlled asymmetric induction: H. Sasai et al., Tetrahedron Lett. 34, 855 (1993); R. Chinchilla et al., Tetrahedron: Asymmetry 5, 1393 (1994); R. S. Varma et al., Tetrahedron Lett. 38, 5131 (1997); R. Ballini, G. Bosica, J. Org. Chem. 62, 425 (1997); V. J. Bulbule et al., Tetrahedron 55, 9325 (1999). Catalyst effects: I. Morao, F. P. Cossio, Tetrahedron Lett. 38, 6461 (1997); P. B. Kisanga, J. G. Verkade, J. Org. Chem. 64, 4298 (1999); D. Simoni et al., Tetrahedron Lett. 41, 1607 (2000); C. Palomo et al, Angew. Chem. Int. Ed. 43, 5442 (2004). Review: G. Rosini, Comp. Org. Syn. 2, 321-340 (1991). Cf. Knoevenagel Condensation.