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C‐H Functionalization of Amino Alcohols by Osmium Tetroxide/NMO or TPAP/NMO: Protecting Group‐Free Synthesis of Indolizidines (–)‐223AB and 3‐ epi ‐(–)‐223AB
Author(s) -
Chen WeiLun,
Wang LeeYa,
Li YuJang
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901494
Subject(s) - chemistry , osmium tetroxide , iminium , moiety , osmium , protecting group , alcohol , acetal , stereochemistry , organic chemistry , ion , catalysis , physics , electron microscope , alkyl , ruthenium , optics
The oxidative cyclization of amino alcohols by osmium tetroxide/NMO or tetrapropylammonium perruthenate (TPAP)/NMO was found to provide an N,O‐acetal moiety through the trapping of the resulting iminium ion by the alcohol. These two transformations were demonstrated in the synthesis of indolizidines (–)‐223AB and 3‐ epi ‐(–)‐223AB.