Highly Diastereoselective Synthesis of Fully Substituted Tetrahydrofurans by a One‐Pot Cascade Reaction of Aryldiazoacetates with Allyl Alcohols | Zendy

Xu Xinfang | Zendy; Han Xingchun | Zendy; Yang Liping | Zendy; Hu Wenhao | Zendy

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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.

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