Williamson Ether Synthesis with Phenols at a Tertiary Stereogenic Carbon: Formal Enantioselective Phenoxylation of β-Keto Esters
Williamson Ether Synthesis with Phenols at a Tertiary Stereogenic Carbon: Formal Enantioselective Phenoxylation of β-Keto Esters
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DOI：
10.1002/chem.201502042
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发表时间：
2015-09-28
影响因子：
4.3
通讯作者：
Iwasa, Seiji
中科院分区：
文献类型：
--
作者：
Shibatomi, Kazutaka;Kotozaki, Manato;Iwasa, Seiji
首次描述了α-芳氧基-β-酮酯的对映选择性形成。在刘易斯酸催化下，β-酮酯的对映选择性氯化反应和随后与苯酚的S（N）2反应得到了ee值高达96%的α-芳氧基-β-酮酯，α-氯-β-酮酯的Favorskii重排反应也得到了对映纯度略有降低的1，2-二酯。
The enantioselective formation of alpha-aryloxy-beta-keto esters is described for the first time. Lewis acid catalyzed enantioselective chlorination of beta-keto esters and subsequent S(N)2 reactions with phenols yielded alpha-aryloxy-beta-keto esters with up to 96% ee. Favorskii rearrangement of alpha-chloro-beta-keto esters was also found to give 1,2-diesters with slightly reduced enantiopurity.