Piers' 硼烷原位生成催化的硅烷对糖的选择性 C-O 键断裂。
Selective C-O Bond Cleavage of Sugars with Hydrosilanes Catalyzed by Piers' Borane Generated In Situ.
机构信息
Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon, 305-701, South Korea.
Department of Chemistry, Korea Advanced Institute of Science & Technology (KAIST), Daejeon, 305-701, South Korea.
出版信息
Angew Chem Int Ed Engl. 2017 Oct 23;56(44):13757-13761. doi: 10.1002/anie.201708109. Epub 2017 Oct 2.
Described herein is the selective reduction of sugars with hydrosilanes catalyzed by using Piers' borane [(C F ) BH] generated in situ. The hydrosilylative C-O bond cleavage of silyl-protected mono- and disaccharides in the presence of a (C F ) BH catalyst, generated in situ from (C F ) BOH, takes place with excellent chemo- and regioselectivities to provide a range of polyols. A study of the substituent effects of sugars on the catalytic activity and selectivity revealed that the steric environment around the anomeric carbon (C1) is crucial.
本文描述了使用 Piers 硼烷 [(CF3)BH] 原位生成的硅烷作为催化剂，选择性还原糖。在 (CF3)BH 催化剂的存在下，通过 (CF3)BOH 原位生成，硅基保护的单糖和二糖的硅烷化 C-O 键断裂具有极好的化学和区域选择性，生成一系列多元醇。对糖的取代基效应对催化活性和选择性的影响的研究表明，在 C1 位的立体环境是至关重要的。
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