1072916-81-4Relevant articles and documents
Stereoselective organocatalytic one-pot α,α-bifunctionalization of acetaldehyde by a tandem mannich reaction/electrophilic amination
Coeffard, Vincent,Desmarchelier, Alaric,Morel, Benedicte,Moreau, Xavier,Greck, Christine
supporting information; experimental part, p. 5778 - 5781 (2012/01/06)
The first asymmetric organocatalyzed one-pot α,α- bifunctionalization of acetaldehyde with two different electrophiles is described. A diarylprolinol silyl ether-catalyzed reaction of acetaldehyde with an imine and di-tert-butyl azodicarboxylate affords s
Asymmetric synthesis of maraviroc (UK-427,857)
Zhao, Gui-Ling,Lin, Shuangzheng,Korotvicka, Ales,Deiana, Luca,Kullberg, Martin,Cordova, Armando
supporting information; experimental part, p. 2291 - 2298 (2010/12/20)
The asymmetric synthesis of Maraviroc (UK-427,857), a chemochine receptor 5 (CCR-5) receptor antagonist, based on an expeditious organocatalytic enantioselective assembly of the chiral βamino aldehyde key fragment is presented. The reactions were performed on a gram-scale and allow for the rapid construction of new Maraviroc analogues.
β-Amidoaldehydes via oxazoline hydroformylation
Laitar, David S.,Kramer, John W.,Whiting, Bryan T.,Lobkovsky, Emil B.,Coates, Geoffrey W.
supporting information; experimental part, p. 5704 - 5706 (2010/01/31)
4-Substituted oxazolines, which are readily synthesized from naturally occurring α-amino acids, are converted efficiently and stereospecifically to β-amidoaldehydes in the presence of synthesis gas and catalytic dicobalt octacarbonyl.
Direct organocatalytic Mannich reaction of acetaldehyde: An improved catalyst and mechanistic insight from a computational study
Hayashi, Yujiro,Okano, Tsubasa,Itoh, Takahiko,Urushima, Tatsuya,Ishikawa, Hayato,Uchimaru, Tadafumi
supporting information; experimental part, p. 9053 - 9058 (2009/02/08)
(Chemical Equation Presented) A chiral diaryl prolinol silyl ether organocatalyst with an acidis used for the direct catalytic asymmetric Mannich reaction of acetaldehyde and imines. N-Benzoyl-, N-tert-butoxycarbonyl-, and N-toluene-4-sulfonylimines can be employed to produce synthetically useful β-amino aldehydes in goodyield s andwith excellent enantioselectivity (see scheme). The reaction mechanism was investigated quantum-mechanically.