170937-77-6Relevant academic research and scientific papers
Hybrid-Type Squaramide-Fused Amino Alcohol Organocatalysts for Enantioselective Nitro-Aldol Reaction of Nitromethane with Isatins
Chennapuram, Madhu,Subba Reddy,Seki, Chigusa,Okuyama, Yuko,Kwon, Eunsang,Uwai, Koji,Tokiwa, Michio,Takeshita, Mitsuhiro,Nakano, Hiroto
, p. 1638 - 1646 (2017)
A series of hybrid-type squaramide-fused amino alcohol (SFAA) catalysts were synthesized, and their catalytic efficiency in the enantioselective nitro-aldol reaction of various isatins with nitromethane has been described. This transformation afforded chiral 3-substituted 3-hydroxyoxindoles in excellent chemical yields (up to 99 %) with high enantioselectivities (up to 95 % ee). The resulting chiral 3-hydroxyoxindoles can be further used as synthetic precursors for the synthesis of several natural products that have a broad spectrum of fascinating biological activities.
A Diamino Alcohol Catalyzed Enantioselective Crossed Aldol Reaction of Acetaldehyde with Isatins – A Concise Total Synthesis of Antitumor Agents
Subba Reddy, Ummareddy Venkata,Chennapuram, Madhu,Seki, Kento,Seki, Chigusa,Anusha, Bheemreddy,Kwon, Eunsang,Okuyama, Yuko,Uwai, Koji,Tokiwa, Michio,Takeshita, Mitsuhiro,Nakano, Hiroto
, p. 3874 - 3885 (2017/07/22)
Enantioselective crossed aldol reactions of isatin derivatives and acetaldehyde have been developed with a series of simple diamino alcohol catalysts to afford 3-substituted 3-hydroxyindolin-2-ones in high chemical yields (up to 95 %) and optical purities (up to 92 % ee). The synthetic potential of the present protocol has been demonstrated by concise, enantioselective, protecting-group-free, and transition metal-free total syntheses of antitumor and antiviral agents with the tryptanthrin architecture, that is, phaitanthrin B and cephalanthrin A, along with the biologically active indolidine alkaloids chimonamidine and donaxaridine as well as the formal synthesis of CPC-1. The highly enantioselective outcome of this catalytic crossed aldol reaction was evaluated by calculating the Gibbs free energies of the possible transition states.
Synthesis of chiral C/N-functionalized morpholine alcohols: Study of their catalytic ability as ligand in asymmetric diethylzinc addition to aldehyde
Dave, Rajesh,Sasaki, N. Andre
, p. 388 - 401 (2007/10/03)
A broad variety of chiral C/N-functionalized morpholine alcohols sharing a common structural motif in the 3-(hydroxymethyl)morpholine 6 were prepared from enantiomerically pure serine for the purpose of studying their catalytic ligand properties. The asym
Stereocontrolled Conversion of L-Serine into a Series of Valuable Unnatural α-Amino Acids
Koskinen, Ari M. P.,Hassila, Heikki,Myllymaeki, Vesa T.,Rissanen, Karl
, p. 5619 - 5622 (2007/10/02)
Stereocontrolled synthesis of (2R,3S)- and (2R,3R)-phenylserine, (R)-3,3-diphenylserine and (R)-3,3-diphenylalanine are described.
