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Asymmetric Conjugate Addition of Acetylacetone to Nitroolefins with Chiral Organocatalysts Derived from Both α‐Amino Acids and Carbohydrates
Author(s) -
Pu Xuewei,
Li Penghui,
Peng Fangzhi,
Li Xiaojiao,
Zhang Hongbin,
Shao Zhihui
Publication year - 2009
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.200900547
Subject(s) - chemistry , acetylacetone , enantioselective synthesis , enantiomeric excess , conjugate , organic chemistry , bifunctional , enantiomer , organocatalysis , amine gas treating , catalysis , mathematical analysis , mathematics
Bifunctional chiral tertiary amine thioureas derived from both α‐amino acids and carbohydrates were developed. These organocatalysts promoted the enantioselective conjugate addition of acetylacetone to various aromatic and aliphatic nitroolefins at room temperature in good yields (up to 93 %) and with good enantioselectivity (up to 90 % ee ). Furthermore, an interesting matched–mismatched effect of two different chiral units in a chiral organocatalyst was disclosed. Both enantiomers of a product can be achieved in almost the same enantiomeric excess with the “matched” and “mismatched” chiral organocatalysts simply by changing the solvent from THF to toluene. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)