Highly Enantioselective Organocatalytic Formation of Functionalized Cyclopentane Derivatives via Tandem Conjugate Addition/α‐Alkylation of Enals | Zendy

Remeš Marek | Zendy; Veselý Jan | Zendy

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Highly Enantioselective Organocatalytic Formation of Functionalized Cyclopentane Derivatives via Tandem Conjugate Addition/α‐Alkylation of Enals

Author(s) -

Remeš Marek,

Veselý Jan

Publication year - 2012

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201200334

Subject(s) - enantioselective synthesis , chemistry , alkylation , cyclopentane , cyclopentanes , catalysis , conjugate , tandem , amine gas treating , organocatalysis , organic chemistry , cascade reaction , selectivity , medicinal chemistry , mathematical analysis , materials science , mathematics , composite material

An enantioselective tandem reaction between dialkyl 2‐haloethylmalonates and aromatic enals catalyzed by secondary amine catalysts is described. The reaction proceeds through a Michael/α‐alkylation reaction sequence to afford the final 1,1,2,3‐tetrasubstituted cyclopentanes in good yields (up to 75 %) with high diastereoselectivity and enantioselectivity (up to 20:1 dr and 93 % ee ). Moreover, the Michael/α‐alkylation reaction also proceeds with a low catalyst loading (5 mol‐%) with only a slight influence on selectivity and O ‐ and N ‐alkylation products were not observed.

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