An Organocatalytic Asymmetric Tandem Reaction for the Construction of Bicyclic Skeletons

• Published in: Chemistry : a European journal Vol. 15; no. 42; pp. 11384 - 11389
• Main Authors: Cao, Chun-Li, Zhou, You-Yun, Zhou, Jian, Sun, Xiu-Li, Tang, Yong, Li, Yu-Xue, Li, Guang-Yu, Sun, Jie
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 26.10.2009; WILEY‐VCH Verlag; Wiley
• Subjects: bifunctional catalysts; Chemistry; Chemistry, Multidisciplinary; density functional calculations; ketones; organocatalysis; Physical Sciences; Science & Technology; tandem reactions; 4 STEREOCENTERS; CATALYSIS; DOMINO REACTIONS; ALPHA,BETA-UNSATURATED ALDEHYDES; MULTISUBSTITUTED CYCLOPENTANES; HENRY REACTION; ketones; organocatalysis; density functional calculations; MICHAEL-ALDOL REACTIONS; TRICYCLIC CARBON FRAMEWORKS; bifunctional catalysts; STEREOGENIC CENTERS; tandem reactions

Cyclic ketones react with (E)‐2‐nitroallylic acetates in the presence of catalytic pyrrolidine‐thiourea, which affords bicyclic skeletons with four or five stereocenters in one single reaction with up to 98 % ee in moderate to high yields. The cooperative effects of both enamine and the Brønsted aci...