Enantioselective Phase-Transfer Catalyzed 伪-Sulfanylation of Isoxazolidin-5-ones: An Entry to 尾2,2-Amino Acid Derivatives was written by Cadart, Timothee;Berthonneau, Clement;Levacher, Vincent;Perrio, Stephane;Briere, Jean-Francois. And the article was included in Chemistry – A European Journal in 2016.COA of Formula: C37H37BrN2O This article mentions the following:
An unprecedented enantioselective 伪-functionalization of C4-substituted N-alkoxycarbonyl isoxazolidin-5-ones, readily available platforms from Meldrum’s acid derivatives, by N-sulfanylphthalimide (PhthSR) electrophiles was achieved upon an efficient phase-transfer catalytic approach, mediated by a com. N-spiro quaternary ammonium catalyst. Two catalytic activities of the in situ formed R4N+Phth– species were highlighted, the phtalimidate being involved in the anion metathesis event and likely as a Bronsted base. This sequence offers a straightforward access to 伪,伪-disubstituted isoxazolidinones, which turned out to be useful precursors of 伪-sulfanyl-尾2,2-amino acid derivatives 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: 200132-54-3COA of Formula: C37H37BrN2O).
(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. Quinuclidine acts as a catalyst, a chemical building block and is used in organic synthesis. Asymmetric construction of quinuclidine derivatives has been realized by an iridium-catalyzed allylic dearomatization reaction. The catalytic system, derived from [Ir(cod)Cl]2 and the Feringa ligand, tolerates a broad range of substrates. A large array of quinuclidine derivatives can be obtained under mild conditions in good to excellent yields (68%鈥?6%), diastereoselectivity (up to >20/1 dr), and enantioselectivity (up to >99% ee).COA of Formula: C37H37BrN2O
Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider