Asymmetric Synthesis of β-Hydroxy Amino Acids via Aldol Reactions Catalyzed by Chiral Ammonium Salts was written by Mettath, Sashikumar;Srikanth, G. S. C.;Dangerfield, Benjamin S.;Castle, Steven L.. And the article was included in Journal of Organic Chemistry in 2004.Safety of (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide This article mentions the following:
The cinchona alkaloid-derived chiral ammonium salt developed by Park and Jew functions as an effective catalyst for the synthesis of β-hydroxy α-amino carboxylic acids via asym. aldol reactions under homogeneous conditions. The syn diastereomers are obtained in good ee, and aryl-substituted aliphatic aldehydes are the best substrates for the reaction. These results represent the highest ee’s obtained to date in direct aldol reactions of glycine equivalent catalyzed by inexpensive, readily prepared chiral ammonium salts. The (+)-10,11-dihydro-9-(2-propenyloxy)-1-[(2,3,4-trifluorophenyl)methyl]cinchonanium bromide (I) was prepared from dihydrocinchonine, trifluorobenzyl bromide, and allyl bromide. I was evaluated as stereoselective catalyst for the aldol condensation of benzenepropanal with N-(diphenylmethylene)glycine 1,1-dimethylethyl ester. In the experiment, the researchers used many compounds, for example, (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3Safety of (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide).
(1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide (cas: 200132-54-3) belongs to quinuclidine derivatives. In alkane solvents quinuclidine is a Lewis base that forms adducts with a variety of Lewis acids. Traditionally, quinuclidine scaffolds can be constructed by second-order nucleophilic substitution (SN2) reaction or condensation reaction of piperidine derivatives. However, most of these reactions are racemic or chiral auxiliary-assisted processes.Safety of (1S,2S,4S,5R)-2-((R)-(Allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide
Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider