Hosomi-Sakurai Reaction

Schematic representation of the Hosomi-Sakurai Reaction.

Mechanism of the Hosomi-Sakurai Reaction

Mechanism of the Hosomi-Sakurai Reaction

Original publication	Tetrahedron Lett.. 1976, 17, 1295.
Reviews	Acc. Chem. Res.. 1988, 21, 200. Comp. Org. Syn.. 1991, 2, 563. Org. React.. 1989, 37, 57.

Sample reactions

intermediate structure

intermediate structure

NaBH3CN, (CF3CO)2O

MeCN

0 °C to RT, 2.5 h, 66%

intermediate structure

intermediate structure

BF3.OEt2, AllylTMS

CH2Cl2

0 °C, 60 min, 72%

intermediate structure

intermediate structure

intermediate structure

ZnI2

EtOH

60 °C, , 82%

intermediate structure

intermediate structure

intermediate structure

TiCl4

CH2Cl2

71%

intermediate structure

intermediate structure

TiCl4

CH2Cl2

-78 °C, 60 min, 72%

intermediate structure

intermediate structure

ZnCl2

CHCl3

Reflux, 30 min, 93%

intermediate structure

intermediate structure

TsOH

CHCl3

RT to reflux, 30 min, 96%

intermediate structure

intermediate structure

EtAlCl2

PhMe

0 °C, 77%

intermediate structure