化学
产量(工程)
羧酸
结合
锂(药物)
立体化学
顺反异构
药物化学
有机化学
数学
医学
内分泌学
数学分析
冶金
材料科学
作者
Mark E. Bunnage,Stephen G. Davies,Paul M. Roberts,Andrew D. Smith,Jonathan M. Withey
摘要
The diastereoselective conjugate addition of lithium (S)-N-benzyl-N-α-methylbenzylamide has been successfully applied to the first asymmetric syntheses of cis-(3S,4R)- and trans-(3R,4R)-4-aminotetrahydrofuran-3-carboxylic acids (26% and 25% overall yield respectively, >98% d.e. and >97% e.e. in each case). Furthermore, the most efficient asymmetric synthesis to date of cis-(3R,4R)- and trans-(3R,4S)-4-aminopyrrolidine carboxylic acids is delineated: for cis-(3R,4R), four steps, >98% d.e., 52% overall yield; for trans-(3R,4S), five steps, >98% d.e., 50% overall yield.
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