Synthesis 2020; 52(06): 807-818
DOI: 10.1055/s-0039-1690046
short review
© Georg Thieme Verlag Stuttgart · New York

Transition-Metal-Catalyzed Annulative Coupling Cascade for the Synthesis of 3-Methyleneisoindolin-1-ones

Center for New Directions in Organic Synthesis, Department of Chemistry and Research Institute for Natural Sciences, Hanyang University, Seoul 04763, Republic of Korea   Email: [email protected]
› Author Affiliations
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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