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. 2009 Mar 11;131(9):3122-3.
doi: 10.1021/ja809873u.

Catalytic enantioselective synthesis of tetrahydrofurans: a dynamic kinetic asymmetric [3 + 2] cycloaddition of racemic cyclopropanes and aldehydes

Andrew T Parsons  1 , Jeffrey S Johnson
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Catalytic enantioselective synthesis of tetrahydrofurans: a dynamic kinetic asymmetric [3 + 2] cycloaddition of racemic cyclopropanes and aldehydes

Andrew T Parsons et al. J Am Chem Soc. .

Abstract

A highly diastereoselective dynamic kinetic asymmetric transformation of racemic 1,1-cyclopropane diesters to prepare enantioenriched tetrahydrofuran (THF) derivatives has been developed. Asymmetric [3 + 2] cycloaddition of activated donor-acceptor (D-A) cyclopropanes and aldehydes catalyzed by ((t)Bu-pybox)MgI(2) gives THF products in good to excellent yields (48-92%) as single diastereomers with er's up to 97:3. Aryl, cinnamyl, and aliphatic aldehydes are competent dipolarophiles for this transformation.

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