Enantioselective α-hydrazination of α-fluoro-β-ketoesters catalyzed by chiral nickel complexes

Enantioselective Michael Addition of 3-Aryl-Substituted Oxindoles to Methyl Vinyl Ketone Catalyzed by a Binaphthyl-Modified Bifunctional Organocatalyst

“…As part of the research program related to the development of synthetic methods for the catalytic carbon-carbon bond formations [ 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 ], we recently reported the organocatalytic conjugate addition reactions of α,β-unsaturated carbonyl compounds [ 51 , 52 , 53 ] and other Michael acceptors [ 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 ]. In this Communication, we wish to describe the enantioselective conjugate addition reaction of 3-substituted oxindoles with methyl vinyl ketone catalyzed by binaphthyl-modified bifunctional organocatalysts bearing both central and axial chiral elements.…”

Highly enantioselective conjugate addition of fluoromalonates to nitroalkenes using bifunctional organocatalysts

“…As part of research program related to the development of synthetic methods for the enantioselective construction of stereogenic carbon centers [41,[43][44][45][46][47][48][49][50], we recently reported chiral amine-thiourea I (Fig. 1) to be a highly selective catalyst for the enantioselective amination of active methines [51,52].…”

Recent Advances in Catalytic Enantioselective Synthesis of Fluorinated α‐ and β‐Amino Acids

“…[23] Three years later, by using air-and moisture-stable chiral nickel catalyst 13, the Kim group reported the same amination with t-butyl azodicarboxylate 10 c, albeit with modest ee values. [24] Recently, Vallribera and Sodupe found that the use of chiral Pybox 14 ligated Eu(OTf) 3 was also efficient to catalyze the same amination reaction, furnishing the target with excellent enantioselectivity. [25] Chiral organocatalysis also demonstrated their powerfulness in the asymmetric amination of α-fluoroβ-keto esters 9 toward optically active α-amino-α-fluoro-β-ketoesters 11 (Scheme 2).…”