A dramatic synergistic effect of a flexible achiral linker on a rigid chiral cis-1, 2-diamine bifunctional organocatalyst. Issue 14 (30th January 2017)

• Record Type: Journal Article
• Authors: Matsunaga, Hirofumi; Tajima, Daisuke; Kawauchi, Tetsuro; Yasuyama, Takuro; Ando, Shin; Ishizuka, Tadao
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 14(2017)
• Page Start: 2892
• Page End: 2896
• Publication Date: 2017-01-30
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob02743a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The combination of a "rigid" chiral bicyclic cis -1, 2-diamine skeleton and a "flexible" achiral linker was newly designed as a bifunctional organocatalyst framework and showed excellent catalytic activity, accompanied by the reversal of enantioselection. Abstract : The combination of a "rigid" chiral bicyclic cis -1, 2-diamine skeleton with steric bulkiness and a "flexible" achiral linker was newly designed as a bifunctional organocatalyst framework and it showed excellent catalytic activity of up to 0.05 mol%, accompanied by the reversal of enantioselection depending on the position of the linker, in an amine-thiourea organocatalyzed asymmetric Michael reaction.