ja055776k_si_002.cif (15.97 kB)

Preorganization in Highly Enantioselective Diaza-Cope Rearrangement Reaction

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posted on 30.11.2005, 00:00 by Hae-Jo Kim, Hyunwoo Kim, Gamil Alhakimi, Eui June Jeong, Nirusha Thavarajah, Lisa Studnicki, Alicja Koprianiuk, Alan J. Lough, Junghun Suh, Jik Chin
Crystal structure and activation entropy data indicate that H-bond directed diaza-Cope rearrangement of chiral diimines takes place with a high degree of preorganization. CD spectroscopy and HPLC data show that there is inversion of stereochemistry for the reaction with excellent enantioselectivity.