133615-53-9Relevant articles and documents
Dimethylamine adducts of allylic triorganoboranes as effective reagents for Petasis-type homoallylation of primary amines with formaldehyde
Kuznetsov, Nikolai Yu.,Tikhov, Rabdan M.,Strelkova, Tatiana V.,Bubnov, Yuri N.
, p. 7115 - 7119 (2018)
Dimethylamine adducts of triallyl-, triprenyl- and trans-cinnamyl(dipropyl)borane are effective reagents for mild homoallylation of primary amines with aqueous formaldehyde in MeOH without an inert atmosphere. A new concept is proposed for the explanation of the high stability of allylborane-amine adducts in aqueous MeOH.
Stereoselective multicomponent assembly of enantiopure oxazolopiperidines and -azepines
Zill, Nicolas,Schoenfelder, Angele,Girard, Nicolas,Taddei, Maurizio,Mann, Andre
experimental part, p. 2246 - 2253 (2012/05/20)
A multicomponent reaction (MCR) based on a cyclohydrocarbonylation (CHC) driven by hydroformylation was set up toward the efficient diastereoselective preparation of oxazolopiperidines (4a-e) and -azepines (7a-d). The bicyclic oxazolidines were obtained from chiral N-alkenylamino alcohols via transient cyclic iminium intermediates that underwent an intramolecular cyclization from the appendant oxygen. On the basis of a series of different experimental conditions, the diastereocontrol observed during the formation of the oxazolidines is best explained by the stereoelectronic effect induced by an A1,3-strain in a common cyclic iminium intermediate (A). This new sequence is suitable for diversity oriented syntheses, allowing the preparation of enantiopure (S)- and (R)-coniceine in five steps from commercially available material.
Asymmetric Synthesis of Pipecolic Acid Derivatives
Agami, Claude,Couty, Francois,Poursoulis, Michel,Vaissermann, Jacqueline
, p. 431 - 442 (2007/10/02)
Condensation of chiral N-homoallyl β-amino alcohols with glyoxal produces iminium ions which are cyclized with complete stereoselectivity.These substrates, whose reactivity is closely dependent on the substitution pattern of the ethylenic moiety, undergo