An α-selective, visible light photocatalytic glycosylation of alcohols with selenoglycosides
An α-selective, visible light photocatalytic glycosylation of alcohols with selenoglycosides
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DOI：
10.1016/j.carres.2013.01.004
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发表时间：
2013-03-22
影响因子：
3.1
通讯作者：
Ragains, Justin
中科院分区：
文献类型：
--
作者：
Spell, Mark;Wang, Xiaoping;Ragains, Justin
已经开发了在酒精受体存在下对硒糖苷供体进行可见光催化活化的异常温和的方法。1-苯基-2，3，4，6-四-O-苯基葡萄糖苷(1)和1-苯基-2，3，4，6-四-O-苯基半乳糖苷(2)证明了这一过程。金属催化剂(Ru(Bpy)(3))和有机催化剂(二苯基二硒醚)都能起到催化作用。在所有情况下，反应提供的主要是具有选择性的α-异构体，选择性因溶剂而异。这是可见光促进O-糖基化的第一个例子。(C)2013爱思唯尔有限公司。保留所有权利。
Exceptionally mild procedures for the visible light photocatalytic activation of selenoglycoside donors in the presence of alcohol acceptors have been developed. This process is demonstrated with both 1-phenylselenyl-2,3,4,6-tetra-O-benzyl glucoside (1) and 1-phenylselenyl-2,3,4,6-tetra-O-benzyl galactoside (2). Catalysis is effected with both metal (Ru(bpy)(3)) and organocatalysts (diphenyldiselenide). Reactions afford, in all cases, primarily the alpha-anomers with selectivities that vary with solvent. This represents the first example of a visible light-promoted O-glycosylation. (C) 2013 Elsevier Ltd. All rights reserved.