Tetrahedron Asymmetry p. 1873 - 1874 (1994)
Update date:2022-08-23
Topics:
Ribeiro, Leny P.
Antunes, Octavio A. C.
Bergter, Lothar
Costa, Paulo R. R.
The stereoselectivities of the reaction between 1-menthylpropionate 1 with LDA under standard kinetic conditions depend on the solvent.The Z-enolate 2a predominates in LDA/THF (Z/E=7.5/2.5) while the E-enolate 3a is the main product in LDA/THF/hexane (E/Z=8/2).The mixture of these enolates (E/Z=8/2) was allowed to react with allylbromide, benzaldehyde and MoOPH respectively.The higher ?-facial diastereoselection was obtained from MoOPH (d.e.=60percent).
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