1206727-07-2Relevant academic research and scientific papers
Intermolecular alkyl radical additions to enantiopure N-tert-butanesulfinyl aldimines
Fernandez-Salas, Jose A.,Maestro, M. Carmen,Rodriguez-Fernandez, M. Mercedes,Garcia-Ruano, Jose L.,Alonso, Ines
supporting information, p. 1658 - 1661 (2013/06/26)
The sulfinyl group in (R)-N-tert-butanesulfinyl aldimines provides efficient control of the stereoselectivity in the intermolecular reactions with alkyl radicals. The methodology is applicable to aryl, heteroaryl, benzyl, and alkynyl imines, even those containing CN, CO2Me, COR, and OH groups. The best results are attained with hindered radicals (tertiary and secondary ones) without C=N bond reduction. This reaction complements the well-established organometallic additions to N-sulfinyl aldimines to obtain enantiomerically pure functionalized α-branched primary amines.
Highly diastereoselective addition of alkynylmagnesium chlorides to N-tert-butanesulfinyl aldimines: A practical and general access to chiral α-branched amines
Chen, Bai-Ling,Wang, Bing,Lin, Guo-Qiang
experimental part, p. 941 - 944 (2010/07/13)
(Chemical Equation Presented) The addition of alkynylmagnesium chlorides to N-tert-butanesulfinyl imines proceeded with a remarkably high diastereoselectivity (dr > 13:1, mostly diastereopure), and with a general scope of both reaction partners. The high dr translated into simplified purification and higher optical purity for the synthesis of a wide array of chiral R-branched amines. The alkyne functionality also provides a multitude of opportunities for further synthetic transformations. The short asymmetric synthesis of (+)-angustureine 7 and (-)-cuspareine 10 was realized with use of this approach.
