Aspartate-catalyzed asymmetric epoxidation reactions
Aspartate-catalyzed asymmetric epoxidation reactions
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DOI：
10.1021/ja073055a
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发表时间：
2007-07-18
影响因子：
15
通讯作者：
Miller, Scott J.
中科院分区：
文献类型：
--
作者：
Peris, Gorka;Jakobsche, Charles E.;Miller, Scott J.
我们报道了由含天冬氨酸肽催化的对映选择性环氧化反应。该策略包括将天冬氨酸羧酸侧链转化为相应的过氧化物。烯烃与活化催化剂的反应使该催化剂再生，该催化剂可能通过碳二亚胺介导的脱水途径进行多次循环。对一类氨基取代烯烃的对映选择性可达92%。
We report enantioselective epoxidation reactions that are catalyzed by aspartic acid-containing peptides. The strategy involves the transient conversion of the aspartate carboxylic acid side chain to the corresponding peracid. Reaction of olefin with the activated catalyst regenerates that catalyst, which may be subjected to multiple turnovers through a carbodiimide-mediated dehydration pathway. Enantioselectivities of up to 92% ee are observed for a class of urethane-substituted olefins.