An enantioselective synthesis of benzylidene-protected syn-3,5-dihydroxy carboxylate esters via osmium, palladium, and base catalysis.
An enantioselective synthesis of benzylidene-protected syn-3,5-dihydroxy carboxylate esters via osmium, palladium, and base catalysis.
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通过锇、钯和碱催化，对映选择性合成亚苄基保护的顺式 3,5-二羟基羧酸酯。
DOI：
10.1002/chin.200129038
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发表时间：
2001
期刊：
影响因子：
5.2
通讯作者：
G. O'Doherty
中科院分区：
文献类型：
--
作者：
T. Hunter;G. O'Doherty
[反应：见原文]。以相应的非手性1,3-二烯酸酯为原料，实现了几种受保护的-3,5-二羟基羧酸酯的对映选择性合成。该路线依赖于对映体和区域选择性Sharpless二羟基化和钯催化还原形成-羟基-1-烯酸盐。得到的-羟基-1-烯酸酯随后在一步中转化为苄基保护的3,5-二羟基羧酸酯。苯基苄基保护的3,5-二羟基羧酸酯的总收率高（25% ~ 51%），对映体过量高（80% ~ 95%）。
[reaction: see text]. The enantioselective syntheses of several protected syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral 1,3-dieneoates. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form delta-hydroxy-1-enoates. The resulting delta-hydroxy-1-enoates are subsequently converted into benzylidene-protected 3,5-dihydroxy carboxylic esters in one step. The benzylidene-protected 3,5-dihydroxy carboxylic esters are produced in good overall yields (25% to 51%) and high enantiomeric excesses (80% to >95%).
有机汞的铑催化甲酰化：在高效多元醇合成中的应用。
影响因子：
5.2
作者：
Sarraf,ST;Leighton,JL
通讯作者：
Leighton,JL