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Stereoselective Construction of Entire Diastereomeric Stereotetrads Based on an Asymmetric Morita–Baylis–Hillman Reaction
Author(s) -
Yoshimura Hikaru,
Ishihara Jun,
Hatakeyama Susumi
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700337
Subject(s) - chemistry , stereocenter , diastereomer , stereoselectivity , cinchona , enantiomer , reagent , benzaldehyde , yield (engineering) , enantioselective synthesis , organic chemistry , atropisomer , baylis–hillman reaction , stereochemistry , adduct , enantiomeric excess , catalysis , materials science , metallurgy
A method for the enantio‐ and diastereoselective construction of all possible stereoisomers of a polypropionate stereotetrad having four contiguous stereogenic centers has been developed. The approach features an iterative sequence of cinchona‐alkaloid‐catalyzed Morita–Baylis–Hillman reaction and subsequent diastereoselective hydrogenation. By this method, benzaldehyde was successfully converted into eight diastereoisomeric 3,5‐dihydroxy‐2,4‐dimethyl‐5‐phenylpentanoic acid ester derivatives with high enantiomeric purities (99 % ee ) in 25–67 % overall yield (eight steps) in a reagent‐controlled manner.