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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.