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Lactols in Asymmetric Sequential Organo‐ and Gold‐Catalysis: Synthesis of Densely Functionalized Epimeric Bicyclic O,O‐Acetals
Author(s) -
You ZhiHao,
Chen YingHan,
Wu XiaoNa,
Liu YanKai
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701071
Subject(s) - chemistry , bicyclic molecule , diastereomer , stereoselectivity , yield (engineering) , catalysis , ring (chemistry) , combinatorial chemistry , molecule , stereochemistry , organic chemistry , materials science , metallurgy
Starting from substituted racemic lactols, the combination of organo/gold catalytic system works extremely well providing epimeric bicyclic O,O‐acetals as 5,6‐, and 6,6‐fused ring systems in good isolated yield with excellent enantioselectivities as pure diastereomers only after simple chromatographic purification. To highlight the synthetic potential, several oxygen‐containing heterocycles were prepared smoothly via a diversity‐oriented sequential process with high regio‐ and stereoselectivity, which are important structural units found in natural products and bioactive unnatural molecules.