A practical synthesis of optically active aromatic epoxides via asymmetric transfer hydrogenation of α-chlorinated ketones with chiral rhodium–diamine catalyst
T Hamada, T Torii, K Izawa, T Ikariya
Index: Hamada, Takayuki; Torii, Takayoshi; Izawa, Kunisuke; Ikariya, Takao Tetrahedron, 2004 , vol. 60, # 34 p. 7411 - 7417
Full Text: HTML
Citation Number: 81
Abstract
A practical method for the synthesis of optically active aromatic epoxides has been developed via the formation of optically active α-chlorinated alcohols and intramolecular etherification. Optically active alcohols with up to 99% ee can be obtained from the asymmetric reduction of aromatic ketones with a substrate/catalyst ratio of 1000–5000 using a formic acid/triethylamine mixture containing a well-defined chiral Rh complex, Cp* RhCl ...
Related Articles:
Dynamic kinetic resolution of racemic β-haloalcohols: direct access to enantioenriched epoxides
[Haak, Robert M.; Tarabiono, Chiara; Janssen, Dick B.; Minnaard, Adriaan J.; De Vries, Johannes G.; Feringa, Ben L. Organic and Biomolecular Chemistry, 2007 , vol. 5, # 2 p. 318 - 323]
[Tanis, Steven P.; Evans, Bruce R.; Nieman, James A.; Parker, Timothy T.; Taylor, Wendy D.; Heasley, Steven E.; Herrinton, Paul M.; Perrault, William R.; Hohler, Richard A.; Dolak, Lester A.; Hester, Matthew R.; Seest, Eric P. Tetrahedron Asymmetry, 2006 , vol. 17, # 14 p. 2154 - 2182]
[Tanis, Steven P.; Evans, Bruce R.; Nieman, James A.; Parker, Timothy T.; Taylor, Wendy D.; Heasley, Steven E.; Herrinton, Paul M.; Perrault, William R.; Hohler, Richard A.; Dolak, Lester A.; Hester, Matthew R.; Seest, Eric P. Tetrahedron Asymmetry, 2006 , vol. 17, # 14 p. 2154 - 2182]
[Tanis, Steven P.; Evans, Bruce R.; Nieman, James A.; Parker, Timothy T.; Taylor, Wendy D.; Heasley, Steven E.; Herrinton, Paul M.; Perrault, William R.; Hohler, Richard A.; Dolak, Lester A.; Hester, Matthew R.; Seest, Eric P. Tetrahedron Asymmetry, 2006 , vol. 17, # 14 p. 2154 - 2182]