107301-61-1Relevant articles and documents
Synthesis of homopropargylamines from 2-cyanoazetidines
Quinodoz,Wright,Drouillat,David,Marrot,Couty
, p. 10072 - 10075 (2016)
2-Cyanoazetidines, easily accessible from β-amino alcohols, undergo ring-cleavage upon reaction with trimethylsilylazide and catalytic amounts of Bu2SnO, to give the corresponding homopropargylamines which are isolated as their N-Boc protected
Iodocarbamation of N-Homopropargyl Carbamates: Mild and Stereoselective Entry to Functionalized Oxazinan-2-ones
Quinodoz, Pierre,Quelhas, Alexandre,Wright, Karen,Drouillat, Bruno,Marrot, Jér?me,Couty, Fran?ois
supporting information, p. 2621 - 2626 (2017/05/19)
An efficient and general iodocarbamation of benzyl N-homopropargylcarbamates has been developed by using iodine as the electrophilic agent. This regio- and stereoselective cyclization yielded (E)-6-iodomethyleneoxazinan-2-ones, which can be further transformed through palladium cross-coupling reactions followed by hydrogenation to produce 1,3-oxazinan-2-ones.
Regioselective Amine–Borane Cyclization: Towards the Synthesis of 1,2-BN-3-Cyclohexene by Copper-Assisted Triazole/Gold Catalysis
Motika, Stephen E.,Wang, Qiaoyi,Akhmedov, Novruz G.,Wojtas, Lukasz,Shi, Xiaodong
supporting information, p. 11582 - 11586 (2016/10/24)
The combination of triazole/gold (TA-Au) and Cu(OTf)2is identified as the optimal catalytic system for promoting intramolecular hydroboration for the synthesis of a six-membered cyclic amine–borane. Excellent yields (up to 95 %) and regioselectivities (5-exo vs. 6-endo) were achieved through catalyst control and sequential dilution. Good functional-group tolerance was attained, thus allowing the preparation of highly functionalized cyclic amine–borane substrates, which could not be achieved using other methods. Deuterium-labeling studies support the involvement of a hydride addition to a gold-activated alkyne with subsequent C?B bond formation.