jo9b02444_si_003.cif (1.07 MB)
Sc(OTf)3‑Catalyzed Chemodivergent Annulations of γ‑Butyrolactone-Fused Cyclopropanes with Anthranils
dataset
posted on 2019-12-13, 15:46 authored by Xingyu Zhang, Manli Feng, Gaosheng Yang, Zhuo ChaiThe Lewis acid-catalyzed annulations between anthranils
and γ-butyrolactone-fused
donor–acceptor cyclopropanes have been developed. Depending
on the anthranils used, such annulations proceeded in a chemodivergent
way to produce either bridged cyclic products via [4 + 3] annulation
or γ-butyrolactone-fused tetrahydroquinoline products via a
cascade process in moderate to high yields. A probable mechanism for
the two reaction pathways has been proposed. The reaction could be
performed on a gram-scale, and the products could be elaborated to
other useful cyclic structures bearing multiple contiguous stereogenic
centers.