Stereodivergent Organocatalytic Intramolecular Michael Addition/Lactonization for the Asymmetric Synthesis of Substituted Dihydrobenzofurans and Tetrahydrofurans | Zendy

Belmessieri Dorine | Zendy; de la Houpliere Alix | Zendy; Calder Ewen D. D. | Zendy; Taylor James E. | Zendy; Smith Andrew D. | Zendy

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Stereodivergent Organocatalytic Intramolecular Michael Addition/Lactonization for the Asymmetric Synthesis of Substituted Dihydrobenzofurans and Tetrahydrofurans

Author(s) -

Belmessieri Dorine,

de la Houpliere Alix,

Calder Ewen D. D.,

Taylor James E.,

Smith Andrew D.

Publication year - 2014

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.201402684

Subject(s) - michael reaction , diastereomer , intramolecular force , chemistry , cinchona , enone , enantioselective synthesis , tetrahydrofuran , stereochemistry , catalysis , organic chemistry , solvent

A stereodivergent asymmetric Lewis base catalyzed Michael addition/lactonization of enone acids into substituted dihydrobenzofuran and tetrahydrofuran derivatives is reported. Commercially available ( S )‐(−)‐tetramisole hydrochloride gives products with high syn diastereoselectivity in excellent enantioselectivity (up to 99:1 d.r. syn / anti , 99 % ee syn ), whereas using a cinchona alkaloid derived catalyst gives the corresponding anti ‐diastereoisomers as the major product (up to 10:90 d.r. syn / anti , 99 % ee anti ).

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