TY - JOUR
T1 - Direct Catalytic Enantio- And Diastereoselective Aldol Reaction Using a Zn-Zn-Linked-BINOL Complex
T2 - A Practical Synthesis of syn-1,2-Diols
AU - Kumagai, Naoya
AU - Matsunaga, Shigeki
AU - Yoshikawa, Naoki
AU - Ohshima, Takashi
AU - Shibasaki, Masakatsu
PY - 2001/5/17
Y1 - 2001/5/17
N2 - matrix presented 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 synlanti 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.
AB - matrix presented 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 synlanti 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.
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U2 - 10.1021/ol015878p
DO - 10.1021/ol015878p
M3 - Article
C2 - 11388861
AN - SCOPUS:0000148255
SN - 1523-7060
VL - 3
SP - 1539
EP - 1542
JO - Organic Letters
JF - Organic Letters
IS - 10
ER -