960595-38-4Relevant academic research and scientific papers
Cu(I)-catalyzed decarboxylative aldol-type and Mannich-type reactions for asymmetric construction of contiguous trisubstituted and quaternary stereocenters
Yin, Liang,Kanai, Motomu,Shibasaki, Masakatsu
, p. 3497 - 3506 (2012)
The catalytic asymmetric decarboxylative aldol-type reaction between aldehydes and cyanocarboxylic acids and Mannich-type reaction between aldimines and cyanocarboxylic acids were developed. α,α,β-Trisubstituted- β-hydroxy nitriles bearing contiguous all-carbon quaternary and trisubstituted stereocenters were produced with moderate enantio- and diastereoselectivity in the presence of 10 mol % CuOAc-TANIAPHOS (or DTBM-SEGPHOS) complex in the aldol-type reaction. α,α,β- Trisubstituted-β-amino nitriles containing contiguous all-carbon quaternary and trisubstituted stereocenters were produced with moderate to high enantio- and diastereoselectivity using 5 mol % CuOAc-(R)-DTBM-SEGPHOS complex in the Mannich-type reaction. These reactions proceed through Cu(I)-catalyzed decarboxylative nucleophile generation, followed by the addition of the resulting chiral Cu-ketenimide to aldehydes or imines. Because the reactions proceed under very mild conditions at nearly neutral pH, the reactions are applicable to a wide range of substrate combinations, including both aromatic and aliphatic substrates. Finally, α,α,β-trisubstituted-β- amino nitriles were converted to β2,2,3-amino acid derivatives through simple acidic hydrolysis without any racemization and epimerization.
Enantioselective construction of quaternary stereogenic carbon atoms by the lewis base catalyzed additions of silyl ketene imines to aldehydes
Denmark, Scott E.,Wilson, Tyler W.,Burk, Matthew T.
supporting information, p. 9268 - 9279 (2014/08/05)
Silyl ketene imines derived from a variety of α-branched nitriles have been developed as highly useful reagents for the construction of quaternary stereogenic centers via the aldol addition reaction. In the presence of SiCl4 and the catalytic a
Enantioselective construction of quaternary stereogenic carbons by the Lewis base catalyzed additions of silyl ketene imines to aldehydes
Denmark, Scott E.,Wilson, Tyler W.,Burk, Matthew T.,Heemstra Jr., John R.
, p. 14864 - 14865 (2008/09/18)
Silyl ketene imines derived from a variety of α-branched nitriles have been developed as highly useful reagents for the construction of quaternary stereogenic centers via the aldol addition reaction. In the presence of SiCl4 and the catalytic a
