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Enantioselective Dearomative [3+2] Annulation of 3‐Hydroxymaleimides with Azonaphthalenes
Author(s) -
Zhang Jiayan,
Liu Min,
Huang Min,
Li Wenzhe,
Zhang Xiaomei
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202100722
Subject(s) - enantioselective synthesis , annulation , squaramide , chemistry , natural product , amine gas treating , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , organocatalysis
Chiral indolines represent important structural motifs in a large number of natural products and pharmaceutics. Chiral succinimideunits are also found in a wide range of natural products and pharmaceutical substances. Herein we report an enantioselective dearomative [3+2] annulation of 3‐hydroxymaleimides with azonaphthalenes using a chiral squaramide‐tertiary amine as catalyst. The reactions afforded a large variety of novel succinimide fused indolines in moderate to good yields (up to 99 %) with generally good enantioselectivities (up to 98 % ee). The absolute configuration of one product was assigned by an X‐ray crystal structural analysis and a plausible reaction mechanism was proposed accordingly. Afterwards, under different conditions, one product was treated with triethylsilane and provided two kinds of reductive products in moderate to good yields with good enantioselectivities.