Organocatalytic regioselective Michael additions of cyclic enones via asymmetric phase transfer catalysis was written by Ceccarelli, Roberto;Insogna, Susanna;Bella, Marco. And the article was included in Organic & Biomolecular Chemistry in 2006.Reference of 69221-14-3 This article mentions the following:
Cyclohexanone and cycloheptanone can be enantioselectively functionalized in the 3-position with up to 92% ee and 87% ee, resp., by the base-promoted dimerization of the corresponding enones using 3,4,5-tri(benzyloxy)benzyl cinchoninium bromide as a new effective catalyst. The enantioselective addition of 2-cyclohexenone with tert-Bu cinnamyl ketone under similar conditions is also studied. In the experiment, the researchers used many compounds, for example, (1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3Reference of 69221-14-3).
(1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3) belongs to quinuclidine derivatives. In alkane solvents quinuclidine is a Lewis base that forms adducts with a variety of Lewis acids. Carbamoyl boranes are generally prepared as adducts with tertiary amines, such as trialkyl amines, pyridine, or quinuclidine, via two synthetic approaches based either on amidation of amine-carboxyborane adducts or on hydrolysis of amine-cyanoboranes.Reference of 69221-14-3
Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider