Direct Catalytic Enantio- and Diastereoselective Aldol Reaction Using a Z-Zn-Linked-BINOL Complex: A Practical Synthesis of syn-1,2-Diols

摘要

The direct catalytic enantio- and diastereoselective aldol reaction with 2-hydroxy-2'-methoxyacetophenone proceeded smoothly using as little as 1 mol % of a dinuclear zinc catalyst, Zn-Zn-linked-BINOL complex 2, to afford α,β-dihydroxy ketones in a highly syn-selective manner (up to syn/anti 97/3) and in excellent yields (up to 95%) and ees (up to 99%). Efficient transformations of the α,β-dihydroxy ketone into an α,β-dihydroxy ester and an α,β-dihydroxy amide via regioselective rearrangements are also described.