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Enantioselective synthesis of hindered cyclic dialkyl ethers via catalytic oxa-Michael/Michael desymmetrization.

ABSTRACT: An asymmetric oxa-Michael/Michael cascade reaction of p-quinols and ?,?-unsaturated aldehydes provides access to hindered dialkyl ethers. A highly enantioselective oxa-Michael addition of a tertiary alcohol precedes an intramolecular cyclohexadienone desymmetrization, which allows for the concomitant formation of four contiguous stereocenters in a single step. The highly functionalized bicyclic frameworks are rapidly obtained from simple starting materials with good diastereoselection and serve as valuable precursors for further manipulation.

SUBMITTER: Corbett MT 

PROVIDER: S-EPMC3964814 | biostudies-literature | 2013 Jul

REPOSITORIES: biostudies-literature

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Enantioselective synthesis of hindered cyclic dialkyl ethers <i>via</i> catalytic oxa-Michael/Michael desymmetrization.

Corbett Michael T MT   Johnson Jeffrey S JS  

Chemical science 20130701 7

An asymmetric oxa-Michael/Michael cascade reaction of <i>p</i>-quinols and α,β-unsaturated aldehydes provides access to hindered dialkyl ethers. A highly enantioselective oxa-Michael addition of a tertiary alcohol precedes an intramolecular cyclohexadienone desymmetrization, which allows for the concomitant formation of four contiguous stereocenters in a single step. The highly functionalized bicyclic frameworks are rapidly obtained from simple starting materials with good diastereoselection and  ...[more]

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