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Highly Diastereoselective Synthesis of Fully Substituted Tetrahydrofurans by a One‐Pot Cascade Reaction of Aryldiazoacetates with Allyl Alcohols
Author(s) -
Xu Xinfang,
Han Xingchun,
Yang Liping,
Hu Wenhao
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200902093
Subject(s) - cascade , intramolecular force , stereoselectivity , chemistry , diazo , catalysis , decomposition , combinatorial chemistry , organic chemistry , medicinal chemistry , chromatography
A cascade of tetrahydrofurans : A one‐pot cascade reaction for the preparation of fully substituted tetrahydrofurans from aryldiazoacetates and allyl alcohols is reported. Rh‐catalyzed diazo decomposition of diazoacetates 1 with a secondary alcohols 2 gave an OH insertion product with excellent diastereoselectivity. Subsequent intramolecular Michael‐type addition produced the desired tetrahydrofurans 3 with excellent stereoselective control.