1579160-08-9Relevant academic research and scientific papers
Stereoselective synthesis of isoquinuclidines through an Aza-[4 + 2] cycloaddition of chiral cyclic 2-amidodienes
Fang, Li-Chao,Hsung, Richard P.
, p. 1826 - 1829 (2014)
A highly stereoselective aza-[4 + 2] cycloaddition of chiral cyclic 2-amidodienes with N-sulfonyl aldimines is described. While this Lewis acid promoted heterocycloaddition provides an efficient strategy for constructing optically enriched isoquinuclidines, it is mechanistically intriguing. The cycloaddition favored the endo-II pathway in the absence of a viable bidentate coordination. This represents an unexpected switch from the anticipated endo-I selectivity obtained in the all-carbon cycloaddition.
