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Phosphine‐Catalyzed (3+2) Annulation of Isoindigos with Allenes: Enantioselective Formation of Two Vicinal Quaternary Stereogenic Centers
Author(s) -
Chan WaiLun,
Tang Xiaodong,
Zhang Fuhao,
Quek Glenn,
Mei GuangJian,
Lu Yixin
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201900758
Subject(s) - stereocenter , enantioselective synthesis , annulation , oxindole , chemistry , phosphine , vicinal , stereochemistry , catalysis , organic chemistry , combinatorial chemistry
Construction of contiguous all‐carbon quaternary stereogenic centers is a long‐standing challenge in synthetic organic chemistry. In this report, a phosphine‐catalyzed enantioselective (3+2) annulation reaction between allenes and isoindigos, containing either two identical or different oxindole moieties, is introduced as a powerful strategy for the construction of spirocyclic bisindoline alkaloid core structures. The reported reactions feature high chemical yields, excellent enantioselectivities, and very good regioselectivities, and are highly useful for creating structurally challenging bisindoline natural products.