Origin of stereochemical reversal in Meyers-type enolate alkylations. Importance of intramolecular Li coordination and solvent effects.
[reaction: see text] The origin of exclusive exo-stereochemistry in the alkylation of Meyers-type enolate 2 has been studied. It was found that the intramolecular complex with a strong Li...O(ring) interaction (the O-complex) may be responsible as the major enolate species in tetrahydrofuran (THF). The transition state of the O-complex leading to exo-stereochemistry is found to be the most favorable process in THF.
Ikuta
Yasuhiro
Y
Department of Life Sciences, Graduate School of Arts and Sciences, The University of Tokyo, Komaba, Meguro-ku, Tokyo 153-8902, Japan.
Tomoda
Shuji
S