Nozaki-Hiyama-Kishi Reaction

Schematic representation of the Nozaki-Hiyama-Kishi Reaction.
Mechanism of the Nozaki-Hiyama-Kishi Reaction
Mechanism of the Nozaki-Hiyama-Kishi Reaction
Original publication
J. Am. Chem. Soc.. 1977, 99, 3179. J. Am. Chem. Soc.. 1986, 108, 5644. J. Am. Chem. Soc.. 1986, 108, 6048.
Reviews
Adv. Synth. Catal.. 2007, 349, 240. Org. React.. 2004, 64, 253.
Sample reactions
info
intermediate structure
CrCl2, NiCl2
DMF
30% (3 steps)
intermediate structure
info
intermediate structure intermediate structure
LiAlH4, CrCl3
THF
0 °C to RT, 5 h, 30%
"Also isolated was the C2-epimer (47 % yield)."
intermediate structure
info
intermediate structure intermediate structure
LiAlH4, CrCl3
THF
0 °C to RT, 3 h, 81%
intermediate structure