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- W2055363528 abstract "Abstract A practical methodology directed to the enantioselective synthesis of polypropionate backbones, available for the synthesis of polyketide natural products, has been developed by iterative enantio- and diastereoselective Lewis acid-promoted aldol reactions, followed by diastereoselective radical debromination reactions. A chiral oxazaborolidinone-promoted aldol reaction of a racemic aldehyde, derived from 2-methyl-1,3-propanediol, with a silylketene acetal from ethyl 2-bromopropionate, resulted in highly enantioselective formation of the corresponding bromo aldol adduct, followed by radical debromination with Bu 3 SnH in the presence of Et 3 B to divergently give syn - and anti -propionate aldols, which are versatile stereotriads. Furthermore, elongation of the propionate units has also been achieved: the BF 3 ·OEt 2 -promoted aldol reaction of chiral syn - and anti -α-methyl-β-protected-oxy aldehydes with the silyl nucleophile proceeded with essentially complete syn -selectivity while the TiCl 4 -promoted aldol reaction resulted in fairly good anti -selectivity. The resulting bromo aldol adducts were divergently debrominated by the radical reduction to give a complete set of stereotetrads." @default.
- W2055363528 created "2016-06-24" @default.
- W2055363528 creator A5004339249 @default.
- W2055363528 date "2003-10-01" @default.
- W2055363528 modified "2023-09-24" @default.
- W2055363528 title "Diastereoselective radical debromination approach toward divergent syntheses of syn- and anti-propionate units, coupled with enantioselective and/or diastereoselective Lewis acid-promoted aldol reactions" @default.
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- W2055363528 doi "https://doi.org/10.1016/j.tetasy.2003.06.005" @default.
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