Bifunctional Brønsted Base Catalyzed [3 + 3] Annulations of Indolin-2-imines and α,β-Unsaturated Imides: An Enantioselective Approach to α-Carbolinones
- 20 July 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 85 (15), 9454-9463
- https://doi.org/10.1021/acs.joc.0c00957
Abstract
Asymmetric construction of α-carbolinones with easily available starting materials has recently attracted considerable attention from the synthesis community, and the development of effective catalysis for this target is in great demand. Here, a bifunctional Brønsted base catalyzed asymmetric [3 + 3] cyclization of indolin-2-imines and α,β-unsaturated N-acylated succinimides was developed by using the strategy of noncovalent bonding catalysis. With this organocatalytic protocol, a variety of tetrahydro-α-carbolinones bearing different substituents were synthesized with up to 99% yield and up to 96:4 er.Keywords
Funding Information
- Department of Science and Technology of Sichuan Province (2017JQ0032, 2019JDJQ0010)
- National Natural Science Foundation of China (21702021, 21871031)
- Sichuan Provincial Key Laboratory of Antibiotics Research and Re-evaluation, Sichuan Industrial Institute of Antibiotics, Chengdu University (ARRLKF18-11, ARRLKF19-04)
- Sichuan Province
- Chengdu City Government
This publication has 65 references indexed in Scilit:
- An overview of the synthetic routes to the best selling drugs containing 6-membered heterocyclesBeilstein Journal of Organic Chemistry, 2013
- Extending the Aminocatalytic HOMO-Raising Activation Strategy: Where Is the Limit?Angewandte Chemie, 2012
- Cinchona alkaloid-based phosphoramide catalyzed highly enantioselective Michael addition of unprotected 3-substituted oxindoles to nitroolefinsChemical Science, 2011
- Chiral N,N′-Dioxides: New Ligands and Organocatalysts for Catalytic Asymmetric ReactionsAccounts of Chemical Research, 2011
- Marine Indole Alkaloids: Potential New Drug Leads for the Control of Depression and AnxietyChemical Reviews, 2010
- Chiral Squaramide Derivatives are Excellent Hydrogen Bond Donor CatalystsJournal of the American Chemical Society, 2008
- Biomimetic Synthesis of Grossularines‐1Angewandte Chemie, 2005
- Two new indoloquinoline alkaloids from cryptolepis sanguinolenta: Cryptosanguinolentine and cryptotackieineJournal of Heterocyclic Chemistry, 1996
- Kapakahine B, a cyclic hexapeptide with an .alpha.-carboline ring system from the marine sponge Cribrochalina olemdaJournal of the American Chemical Society, 1995
- Oxaline and neoxaline.CHEMICAL & PHARMACEUTICAL BULLETIN, 1980