Charette Asymmetric Cyclopropanation

Schematic representation of the Charette Asymmetric Cyclopropanation.
Mechanism of the Charette Asymmetric Cyclopropanation
Mechanism of the Charette Asymmetric Cyclopropanation
Original publication
J. Am. Chem. Soc.. 1994, 116, 2651. ACS Med. Chem. Lett.. 2012, 3, 584.
Reviews
Chem. Rev.. 2003, 103, 977. J. Am. Chem. Soc.. 1998, 120, 11943. Synlett. 1995, 0, 1197.
Sample reactions
info
intermediate structure
Et2Zn, CH2I2
CH2Cl2, DME
-20 °C to RT, 8.5 h, 90%
intermediate structure
info
intermediate structure
Et2Zn, CH2I2
CH2Cl2, DME
-20 °C to RT, 8.5 h, 90%
intermediate structure
info
intermediate structure
Et2Zn, CH2I2
CH2Cl2, DME
-10 °C to RT, 14.5 h, 91%
intermediate structure
info
intermediate structure
Et2Zn, CH2I2
CH2Cl2, DME
-15 °C, 8 h, 99%
intermediate structure
info
intermediate structure
Et2Zn, CH2I2
CH2Cl2, DME
-15 °C, 8 h, 96%
intermediate structure
info
intermediate structure
Et2Zn, CH2I2
CH2Cl2, DME
-20 °C to RT, 8.5 h
intermediate structure
info
intermediate structure
Et2Zn, CH2I2
CH2Cl2, DME
0 °C to RT, 105 min, 88%
"94:06 e.r."
intermediate structure