Highly diastereoselective synthesis of an octahydro-1H-cyclpenta[c]pyridine skeleton via a Pd/Au-relay catalyzed reaction of (Z)-1-iodo-1,6-diene and alkyne

Chi, Xiaochen; Tong, Xia; Yang, Yi; Cao, Tong; Zhang, Daopeng; Liu, Hui

doi:10.1039/d2qo00233g

Cited by 8 publications

(8 citation statements)

References 44 publications

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“…In 2022, the Liu group established a straightforward palladium‐catalyzed copper‐free cascade cyclization of 1,6‐dienes with alkynes, allowing the facile synthesis of various piperidines bearing 1,5‐enyne frameworks in high yields with good substrate tolerance (Scheme 14). [26] It′s worth noting that the Heck/Sonogashira reaction performed well with low palladium catalyst loading and led to the corresponding products with excellent diastereoselectivity.…”

Section: Heck/sonogashira Reactionmentioning

confidence: 99%

Transition‐Metal‐Catalyzed Transformations Involving the Heck Reaction

2023

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Elaborated molecular architectures including complex carbocycles, heterocycles, and polycyclic molecular structures represent an important class of organic compounds because they are ubiquitous structural units in a broad variety of biologically and pharmacologically relevant natural products, medicinal molecules, and functional materials. A major challenge in modern synthetic methodology is the development of strategically efficient and selective construction of these compounds from readily available starting materials. Transition‐metal‐catalyzed transformations involving Heck reaction as the pivotal step have afforded a powerful approach for accessing sophisticated polycyclic skeletons from a set of easy‐to handle starting materials, thus highlighting its potential significance in streamlining the drug discovery process. Over the past few decades, significant effort has been devoted to accessing complex polycyclic derivatives in efficient and versatile routes, and a number of powerful and direct synthetic strategies have been reported. In this review, the latest advances in transition‐metal‐catalyzed transformations involving Heck reaction as the critical step are summarized, which could be divided into six categories: 1) Heck/Sonogashira tandem reaction; 2) Heck/Suzuki tandem reaction; 3) Heck/Heck tandem reaction; 4) Heck/Hiyama tandem reaction; 5) Heck/Cacchi tandem reaction; 6) Heck/C−H bond functionalization tandem reaction.

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Section: Heck/sonogashira Reactionmentioning

confidence: 99%

Transition‐Metal‐Catalyzed Transformations Involving the Heck Reaction

2023

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“…al reported a strategy involving Pd‐catalyzed intramolecular Heck cyclization (Scheme 16). [47] The reaction begins with the reduction of Pd II to Pd 0 in the presence of PPh 3 , followed by oxidative addition to alkenyl iodide 70 to give the intermediate 74 . Then, the Heck‐type cyclization produces the intermediate 75 .…”

Section: Reaction With Alkenementioning

confidence: 99%

“…). [47] The reaction begins with the reduction of Pd II to Pd 0 in the presence of Based on previous experiments, [39] Tong et. al described an effective Pd 0 /phosphinooxazoline (PHOX) catalyst system that facilitated the asymmetric alkenylborylation of (Z)-1-iodo-dienes with B 2 pin 2 in 2017 (Scheme 18).…”

Section: Reaction With Alkenementioning

confidence: 99%

Transition‐Metal‐Catalyzed Cyclization of Alkenyl Iodide

Jia,

Liu,

Xie

et al. 2023

Adv Synth Catal

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Alkenyl iodide, as an essential precursor and structural unit in organic synthesis, has been widely used in the synthesis of natural products, pharmaceutical pesticides and functional materials. The high reactivity of Csp2‐I bond allowing could lead to form C‐M bond via oxidative addition, and then undergoes C‐M bond transformations to construct new chemical bonds. A variety of valuable scaffolds, in particular the cyclic motifs, could be achieved via designing and synthesis the corresponding alkenyl iodide, which makes this strategy to be a hot topic in synthetic chemistry. In this paper, the recent progress of transition metal‐catalyzed cyclization of alkenyl iodides is summarized, and the possible mechanisms for most transformations are described in detail.

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“…In the first place, we introduce the intramolecular Heck type reaction/alkynylation. Since 2014, Li, [39] Qu and Guo, [40] Jiang, [41] Chen, [42] Liu and Zhang, [43] and Zhu and Chen [44] reported a Pd‐catalyzed intramolecular carbo‐alkynylation using terminal alkynes as alkynylating reagents, respectively (Scheme 13a–f). For this type of reaction, the authors proposed a similar mechanism.…”

Section: Introductionmentioning

confidence: 99%

The Alkynylative Difunctionalization of Alkenes

Huang

Chen

2022

Chemistry A European J

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Given alkynyl group is an important functional unit, a variety of efficient methods have been developed to construct alkynyl‐containing compounds. Among them, the alkynylative difunctionalization of alkenes is one of the most straightforward and efficient strategies for preparing these compounds and so has made great progress in recent years, including the catalytic asymmetric manner. However, there is no comprehensive review to summarize these studies. This review is aimed at comprehensively summarizing the alkynylative difunctionalization of alkenes, which is presented in terms of alkynylation‐initiated and alkynylation‐terminated difunctionalizations of alkenes. We hope that this review will help to encourage more researchers to further explore in this field.

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Highly diastereoselective synthesis of an octahydro-1H-cyclpenta[c]pyridine skeleton via a Pd/Au-relay catalyzed reaction of (Z)-1-iodo-1,6-diene and alkyne

Abstract: The Octahydro-1H-cyclopenta[c]pyridine Skeletons exist in a broad spectrum of bioactive natural products, and the development of efficient and convenient protocols to construct this skeleton remains a challenging task. Herein, we...

Cited by 8 publications

References 44 publications

Transition‐Metal‐Catalyzed Transformations Involving the Heck Reaction

Transition‐Metal‐Catalyzed Transformations Involving the Heck Reaction

Transition‐Metal‐Catalyzed Cyclization of Alkenyl Iodide

The Alkynylative Difunctionalization of Alkenes

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