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Synthesis 2020; 52(06): 807-818
DOI: 10.1055/s-0039-1690046
DOI: 10.1055/s-0039-1690046
short review
Transition-Metal-Catalyzed Annulative Coupling Cascade for the Synthesis of 3-Methyleneisoindolin-1-ones
This work was supported by both the Basic Science Research Program and the Nano·Material Technology Department Program through the National Research Foundation of Korea (NRF) funded by the Government of Korea (MSIP) (Grant Nos. 2012M3A7B4049644, 2018R1A2A2A05018392, and 2014-011165).
Further Information
Publication History
Received: 04 October 2019
Accepted after revision: 09 December 2019
Publication Date:
15 January 2020 (online)
Abstract
This short review describes the recent progress made on transition-metal-catalyzed annulative couplings for the synthesis of 3-methyleneisoindolin-1-ones, which are useful intermediates for the synthesis of numerous alkaloids and can be often found in a wide range of natural products and pharmaceuticals. In particular, new one-pot multiple C–C/C–N bond-forming processes for the construction of the 5-methylenepyrrol-2-one nucleus of such compounds are summarized.
1 Introduction
2 Intramolecular Cyclization Reactions: C3–N or C3–C3a and C–C Bond Formation
3 Intermolecular Annulative Coupling Reactions
3.1 C3–C3a and C3–N Bond Formation
3.2 C1–C7a and C3–N Bond Formation
3.3 C1–C7a and C1–N Bond Formation
3.4 C1–C7a, C1–N and C3–N Bond Formation
3.5 C3–C3a, C1–C7a, C1–N and C3–N Bond Formation: A Pd-Catalyzed One-Pot Sonogashira Coupling–Carbonylation–Amination–Cyclization Cascade
4 Conclusion
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For selected reviews, see:
For reviews on C–H functionalizations using an amide directing group, see:
With [Cu]:
With [Co]:
With [Ni]: