Premium
Enantioselective Organocatalytic Domino Oxa‐Michael/Aldol/Hemiacetalization: Synthesis of Polysubstituted Furofuranes Containing Four Stereocenters
Author(s) -
Reyes Efraím,
Talavera Garazi,
Vicario Jose L.,
Badía Dolores,
Carrillo Luisa
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200901333
Subject(s) - stereocenter , domino , enantioselective synthesis , aldol reaction , michael reaction , organocatalysis , amine gas treating , chemistry , organic chemistry , combinatorial chemistry , catalysis
3 in 1 : A triple domino reaction was developed for the preparation of the title products in a single step starting from α,β‐unsaturated aldehydes and dihydroxyacetone dimer using a chiral secondary amine catalyst (see scheme, TMS=trimethylsilyl). The title reaction sequence proceeds with the generation of four stereogenic centers to deliver bicyclic compounds in good yields and excellent diastereo‐ and enantioselectivities.