39672-04-3Relevant articles and documents
Fused N-Heterocycles with Contiguous Stereogenic Centers Accessed by an Asymmetric Catalytic Cascade Reaction of Tertiary Enamides
Zhen, Li,Tong, Shuo,Zhu, Jieping,Wang, Mei-Xiang
, p. 401 - 405 (2020)
We report in this article a cascade reaction strategy for the synthesis of complex N-heterocyclic compounds with contiguous and tetrasubstituted stereogenic carbons. Under the sequential catalysis of a chiral binol–Ti complex and BF3, cyclopentanone-derived tertiary enamides undergo an enantioselective enamine addition to ketone carbonyls followed by diastereoselective trapping of the resulting acyliminiums by electron-rich aryl moieties to furnish four- and five-membered ring-fused N-heterocyclic products as the sole diastereomers in high yields with up to 99 % ee.
Radical cyclisations of imines and hydrazones
Bowman, W. Russell,Stephenson, Peter T.,Terrett, Nicholas K.,Young, Adrian R.
, p. 7959 - 7980 (2007/10/02)
Radical cyclisation of sp3 carbon-centred radicals onto imines and hydrazones provides a new method for the synthesis of 5- and 6-membered ring nitrogen heterocycles. Cyclisation onto the electrophilic carbon of the C=N group and 5-exo stereoelectronic selectivity are the dominating mechanistic parameters. The C-centred radical intermediates were generated from benzeneselenyl precursors using Bu3SnH.
THE PHOTOCHEMICAL OR THERMAL REARRANGEMENT OF OXAZIRANES AS A METHOD IN ALKALOID SYNTHESIS
Kuehne, Martin E.,Parsons, W. H.
, p. 3763 - 3766 (2007/10/02)
The conversion of cyclic ketones to β-arylethyl amine derived imines, their oxidation to oxaziranes and subsequent photochemical rearrangement to N-(β-arylethyl) lactams was probed as a potential method for alkaloid syntheses.
