244641-41-6Relevant academic research and scientific papers
Efficient nitro-aldol reaction using SmI2: A new route to nitro alcohols under very mild conditions
Concellon, Jose M.,Rodriguez-Solla, Humberto,Concellon, Carmen
, p. 7919 - 7922 (2006)
(Chemical Equation Presented) A novel method to obtain racemic 1-nitroalkan-2-ols by reaction of bromonitromethane with a variety of aldehydes and promoted by SmI2 is reported. On the basis of these results, the chiral version has also been per
Generation of functional diversity via nitroaldol condensations of α-aminoacid aldehydes - A new and stereocontrolled route to acyclic 1,3-diamino-2-alcohols
Hanessian, Stephen,Devasthale, Pratik V.
, p. 987 - 990 (1996)
Condensations of N,N-dibenzyl α-amino aldehydes with nitroalkanes mediated by tetrabutylammonium fluoride proceed in excellent yields and selectivities. This affords rapid and stereoselective access to acyclic molecules containing differentiated nitrogen-
Diastereoselective Henry reactions of N,N-dibenzyl α-amino aldehydes with nitromethane catalyzed by enantiopure guanidines
Ma, Dawei,Pan, Qiangbiao,Han, Fushe
, p. 9401 - 9403 (2002)
Several enantiopure guanidines are studied as the catalysts of Henry reactions of N,N-dibenzyl α-amino aldehydes with nitromethane. Good diastereoselectivity is observed in the reactions of L-valine or L-isoleucine derived aldehydes catalyzed by a (R)-1-(
Diastereoselective asymmetric nitro-aldol reaction of α-amino aldehydes under high pressure without catalyst
Misumi, Yukihiro,Matsumoto, Kiyoshi
, p. 1031 - 1033 (2002)
Under pressure, the nitro-aldol reaction of (S)-N,N-dibenzylphenylalaninal and related compounds with nitroalkanes was highly stereoselective (see scheme; R1, R2 = Me, H; R = Ph, Me, iPr, iBu). This reaction is very convenient, as it
Diastereoselective Henry reaction catalyzed by guanidine-thiourea bifunctional organocatalyst
Sohtome, Yoshihiro,Takemura, Nobuko,Iguchi, Toshitsugu,Hashimoto, Yuichi,Nagasawa, Kazuo
, p. 144 - 146 (2006)
A highly diastereoselective Henry reaction (diastereomer ratio of 84:16 to 99:1) of α-substituted aldehydes with nitromethane was developed using guanidine-thiourea bifunctional catalyst 1. N,N-Dibenzyl-protected α-amino aldehydes (2a, 2d-h) and α-hydroxy
Divergent and Diastereoselective Synthesis of α-Monosubstituted and trans -α,β-Disubstituted γ-Lactams from (S)- N, N -Dibenzyl-α-amino Aldehydes via Henry and Michael Reactions
Meirelis, Francine P.,Vieira, Bruna G. N.,Pereira, Vera L. P.
, p. 3650 - 3656 (2020)
γ-Monosubstituted and trans -α,β-disubstituted γ-lactams were diastereoselectively synthesized from common intermediates (S)- N, N -dibenzylated aldehydes derived from natural l -(α)-amino acids, employing a divergent approach. The key features of the rou
A versatile and efficient approach for the synthesis of chiral 1,3-nitroamines and 1,3-diamines via conjugate addition to new (S,E)-Γ-aminated nitroalkenes derived from L-α-amino acids
Pereira, Vera Lucia Patrocinio,Da Silva Moura, Andre Luiz,Vieira, Daniel Pais Pires,De Carvalho, Leandro Lara,Torres, Eliz Regina Bueno,Da Silva Costa, Jeronimo
supporting information, p. 832 - 837 (2013/06/05)
New chiral (S,E)-γ-N,N-dibenzylated nitroalkenes 2a-c were synthesized from natural L-(α)-amino acids in five steps with overall yields of 68-88%. The conjugate addition of hydride, methoxide, nitronate and azide nucleophiles to 2a-c led to the corresponding chiral 1,3-nitroamines in 74-90% yield. The conjugate addition of cyanide anion to 2a,b was followed by HNO2 elimination affording chiral aminated acrylonitriles (73-98%). On the other hand, the azide anion reacted with 2a, in acetonitrile, via a [3 + 2]-cycloaddition in which HNO2 was lost, providing the corresponding 1,2,3-triazole derivative. Direct reduction of 1,3- nitroamine derivatives 9a,b produced the corresponding 1,3-diamines in good yields.
re- and si-face-selective nitroaldol reactions catalyzed by a rigid chiral quaternary ammonium salt: A highly stereoselective synthesis of the HIV protease inhibitor amprenavir (Vertex 478)
Corey,Zhang, Fu-Yao
, p. 1931 - 1934 (2007/10/03)
Either amprenavir (1) or its C(2) diastereomer can be synthesized in a simple way by the use of a nitroaldol reaction carried out in the presence of one or the other of the two ammonium ions 2. The 1,3-diamino-2-hydroxypropyl structural element of 1 is also found in many other peptidomimetics and HIV protease inhibitors. Described here is a new strategy for possible application to direct and stereocontrolled synthesis of such compounds.
