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- W2953144474 abstract "Various examples of highly diastereoselective aldol reactions are presented where the nonracemic lithium enolate 6 derived from a C4-oxygenated vinylogous urethane reacts in syn fashion to provide upon intramolecular lactonization useful γ-alkoxy-δ-lactone synthons 12a−f. In one particular example, the result of reaction with an acrolein surrogate, the lactone product 12e is applied in an efficient asymmetric synthesis of (+)-KDO (10 steps, 34% overall yield). Notable transformations include (1) hydrolysis of the vinylogous urethane functionality, (2) stereoselective reduction of the resulting β-keto-lactone 2, (3) stereoselective dihydroxylation of the vinyl side chain of δ-lactone 17, and (4) addition of α-ethoxy-vinyllithium to the lactone carbonyl of 19 to procure the aldulosonic acid residue in 1 upon ozonolysis." @default.
- W2953144474 created "2019-06-27" @default.
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- W2953144474 date "1998-11-01" @default.
- W2953144474 modified "2023-09-27" @default.
- W2953144474 title "Asymmetric <i>Syn</i>-Selective Aldol Reactions of γ-Oxygenated Vinylogous Urethane with a Second Generation Chiral Auxiliary: Application in Construction of (+)-3-Deoxy-<scp>d</scp>-<i>manno</i>-2-octulosonic Acid" @default.
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- W2953144474 doi "https://doi.org/10.1021/jo981916f" @default.
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