Journal of the American Chemical Society, Vol.135, No.19, 7102-7105, 2013
Asymmetric Induction via Short-Lived Chiral Enolates with a Chiral C-O Axis
A novel method has been developed for the asymmetric cyclization of alkyl aryl ethers. The reactions were assumed to proceed via short-lived chiral enolate intermediates with a chiral C-O axis to give cyclic ethers with tetrasubstituted carbon in up to 99% ee. The half-life of racemization of the chiral enolate intermediate was roughly estimated to be similar to 1 s at -78 degrees C.