Johnson-Corey-Chaykovsky Reaction

Schematic representation of the Johnson-Corey-Chaykovsky Reaction.

Mechanism of the Johnson-Corey-Chaykovsky Reaction

Mechanism of the Johnson-Corey-Chaykovsky Reaction

Original publication	J. Am. Chem. Soc.. 1962, 84, 867. J. Am. Chem. Soc.. 1961, 83, 417. J. Med. Chem.. 2008, 51, 2170.
Reviews	Acc. Chem. Res.. 2004, 37, 611. Chem. Commun.. 2003, 0, 2644. Chem. Rev.. 1997, 97, 2341. Chem. Rev.. 2007, 107, 5841. Tetrahedron. 1987, 43, 2609.

Sample reactions

intermediate structure

Me3SO+ I-, NaH

DMSO

0 °C, 3 h, 91%

intermediate structure

intermediate structure

Me3SO+ I-, NaH

DMSO

RT, 7 h, 54%

intermediate structure

intermediate structure

intermediate structure

t-BuLi

THF

-78 °C, 10 min, 62%

intermediate structure

intermediate structure

TMS2NK, Me3S+ I-

THF

0 °C, 2.5 h, 99%

intermediate structure

intermediate structure

NaH, Me3S+ I-

DMSO

RT, 30 min, 92%

intermediate structure

intermediate structure

Me2S=CH2

91%

intermediate structure

intermediate structure

n-BuLi, Me3S+ I-

THF

-20 °C to RT, 4 h, 70%

intermediate structure

intermediate structure

DMSO, NaH, TMSI

THF

0 °C to RT, 2 h, 61%

intermediate structure