Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 65, Pages 16432-16437Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201704456
Keywords
catalyst dependence; chemoselective; mixed acetal; mukaiyama aldol reaction; stereoconvergent
Categories
Funding
- NRF Nano-Material Technology Development Program [2012M3A7B4049645, 2012M3A7B4049652]
- NRF Basic Research Laboratory Program [2016R1A4A1011451]
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We report a direct, simple, and straightforward approach for the construction of a mixed monosilyl acetal as a new and synthetically valuable functional group by mixing an aldehyde, sodium tert-butoxide, and trimethylsilyl azide. We also demonstrate a catalyst-dependent chemoselective reaction between mixed monosilyl acetals and silyl ketene acetals through Mukaiyama aldol reactions to give different structures of O-protected -hydroxy esters in excellent yields with high chemoselectivities. This study provided the existence of an oxonium ion intermediate and of its kinetically controlled reaction with the pre-equilibrated silyl enol ether obtained from (E)- and (Z)-isomerization.
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