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Organocatalytic Domino Michael–Knoevenagel Condensation Reaction for the Synthesis of Optically Active 3‐Diethoxyphosphoryl‐2‐oxocyclohex‐3‐enecarboxylates
Author(s) -
Albrecht Łukasz,
Richter Bo,
Vila Carlos,
Krawczyk Henryk,
Jørgensen Karl Anker
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200802285
Subject(s) - knoevenagel condensation , michael reaction , domino , chemistry , ether , optically active , organic chemistry , organocatalysis , catalysis , combinatorial chemistry , enantioselective synthesis
Versatile dominoes : A novel, organocatalytic, Michael–Knoevenagel condensation domino reaction of ethyl 4‐diethoxyphosphoryl‐3‐oxobutanoate with various aryl‐ and aliphatic‐substituted α,β‐unsaturated aldehydes catalyzed by a chiral diarylprolinol ether has been successfully performed. The reaction proceeds in a highly enantio‐ and diastereoselective manner giving access to optically active 6‐substituted‐3‐diethoxyphosphoryl‐2‐oxocyclohex‐3‐enecarboxylates (see scheme).A novel, organocatalytic, highly enantio‐ and diastereoselective synthetic approach towards optically active 6‐substituted‐3‐diethoxyphosphoryl‐2‐oxocyclohex‐3‐enecarboxylates is presented. Our methodology utilizes a Michael–Knoevenagel domino reaction sequence of ethyl 4‐diethoxyphosphoryl‐3‐oxobutanoate and α,β‐unsaturated aldehydes catalyzed by a chiral diarylprolinol ether. The cyclohexenecarboxylates obtained are particularly well suited for the preparation of highly functionalized cyclohexene and cyclohexane derivatives, with up to four chiral centers and high levels of stereocontrol.