Peterson Olefination

Schematic representation of the Peterson Olefination.

Mechanism of the Peterson Olefination

Mechanism of the Peterson Olefination

Original publication	J. Org. Chem.. 1968, 33, 780. Tetrahedron. 2005, 61, 5782.
Reviews	Acc. Chem. Res.. 1977, 10, 442. Chem. Soc. Rev.. 2002, 31, 195. Org. React.. 1990, 38, 1. Synthesis. 1984, 0, 384. Top. Curr. Chem.. 1980, 88, 33.

Sample reactions

intermediate structure

PhSCHLiTMS

THF

-23 to 0 °C, 4 h, 64% (2 steps)

intermediate structure

intermediate structure

i-Pr2NLi, TMSCHBrCO2Et

THF

-78 °C, , 70%

intermediate structure

intermediate structure

n-BuLi, TMSCH2CN, B(Oi-Pr)3

THF

-78 °C, 90 min, 67%

"Also isolated was the E-isomer (12 % yield)."

intermediate structure

intermediate structure

intermediate structure

n-BuLi

THF

-15 °C

intermediate structure

intermediate structure

n-BuLi

THF

-74 °C to RT, 8.5 h, 71%

"Also isolated was the E-isomer (12%)"

intermediate structure

intermediate structure

intermediate structure

DBU, n-Bu4N+ F-, (CF3CO)2O

THF

RT to 60 °C, 105 min, 33%

intermediate structure

intermediate structure

n-BuLi, TMSCHN2

-78 to 0 °C, 3.5 h, 83%

intermediate structure