Sequential iodine-mediated diallylsilane rearrangement/asymmetric dihydroxylation: Synthesis and reactions of enantioenriched oxasilacycles

[摘要] Products from an iodine-mediated diallylsilane rearrangement were taken into an asymmetric dihydrox-ylation (AD) reaction resulting in the formation of diastereomeric 6-membered oxasilacycles. Removal of the epimeric stereocenter among this mixture of diastereomers by elimination of iodine produced a sin-gle enantioenriched cyclic allyl silyl ether. The resulting allyl silane was then successfully engaged in sev-eral further transformations, providing an alternative means to prepare useful polyoxygenated intermediates for enantioselective synthesis. (c) 2021 Elsevier Ltd. All rights reserved.

[发布日期] 2021-10-12

[关键词] Diallylsilane;Rearrangement;Asymmetric dihydroxylation;Oxasilacycle;Allylsilane