Henry Reaction

Schematic representation of the Henry Reaction.

Mechanism of the Henry Reaction

Mechanism of the Henry Reaction

Original publication	Compt. Rend.. 1895, 120, 1265. Org. Lett.. 2014, 16, 5874.
Reviews	Angew. Chem. Int. Ed.. 2003, 42, 151. Comp. Org. Syn.. 1991, 2, 321. Symmetry. 2011, 3, 220. Tetrahedron. 2001, 57, 915.

Sample reactions

intermediate structure

Et2NH, MeNO2

EtOH

Reflux, 2.5 h, 68%

intermediate structure

intermediate structure

NH4OAc

MeNO2

Reflux, 60 min, 92%

intermediate structure

intermediate structure

intermediate structure

(S)-BINOL, La(Ot-Bu)3

THF

-50 °C, 60 h, 73%

intermediate structure

intermediate structure

Et3N

MeNO2

RT, 15 h

intermediate structure

intermediate structure

MeNO2, NH4OAc

AcOH

Reflux, 2 h, 65%

intermediate structure

intermediate structure

MeNO2, Cu(OAc)2

EtOH

RT, 5 d, 69%

">99:01 e.r."

intermediate structure

intermediate structure

intermediate structure

i-Pr2NLi

THF

-78 °C to RT, 2.5 h

intermediate structure