Domino 1,4‐ and 1,4‐Addition Reactions of Ketene Silyl Thioacetals to Dialkynyl Imines Promoted by Scandium Triflate: Synthesis of Multifunctionalized δ‐Lactams

Watanabe, Yuya; Isaka, Keisuke; Sato, Koki; Kokado, Shinya; Mizutani, Amane; Hachiya, Iwao

doi:10.1002/ajoc.202100672

Asian J Org Chem

2021

DOI: 10.1002/ajoc.202100672

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Domino 1,4‐ and 1,4‐Addition Reactions of Ketene Silyl Thioacetals to Dialkynyl Imines Promoted by Scandium Triflate: Synthesis of Multifunctionalized δ‐Lactams

Yuya Watanabe

Keisuke Isaka

Koki Sato

et al.

Abstract: Domino 1,4-and 1,4-addition reactions of ketene silyl thioacetals to dialkynyl imines are disclosed. Scandium triflate promoted domino 1,4-and 1,4-addition reactions of ketene silyl thioacetals to dialkynyl imines to give a variety of alkynyl δ-lactams in moderate to good yields.

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Recent Advances in Scandium(III) Triflate Catalysis: A Review

Kumar,

Arora,

Sapra

et al. 2024

Asian J Org Chem

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Over the past three decades, triflate salts have emerged as crucial Lewis acid catalysts in organic synthesis, playing a significant role in cyclization, C‐H bond functionalization, and various other reactions. Among these, rare‐earth triflates have garnered attention due to their water compatibility, environmental friendliness, noncorrosive nature, and reusability. In particular, scandium(III) triflate [Sc(OTf)3] stands out as a water‐resistant Lewis acid with remarkable catalytic activity in aqueous environments. Unlike typical Lewis acids such as AlCl3, BF3, and SnCl4, which are decomposed or deactivated by water, Sc(OTf)3 remains stable and effective. Its exceptional Lewis acidity, resilience against hydrolysis, and recyclability make it a prominent green catalyst. The unique stability of Sc(OTf)3 in water is attributed to the smaller size of scandium ions (Sc3+), enhancing its catalytic efficiency. Sc(OTf)3 has a longstanding history in organic synthesis, facilitating a wide range of reactions including aldol, Michael, allylation, Friedel‐Crafts acylations, Diels‐Alder, Mannich, cycloadditions (including cyclopropanation), and cascade reactions. The increasing utilization of Sc(OTf)3 over the past decade underscores the necessity for updated insights. This review provides a concise overview of the versatility of Sc(OTf)3 as a catalyst, focusing on developments from 2017 to 2024.

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Recent Advances in Scandium(III) Triflate Catalysis: A Review

Kumar,

Arora,

Sapra

et al. 2024

Asian J Org Chem

View full text Add to dashboard Cite

show abstract

Recent progresses in the mechanistic studies of aggregation-induced emission-active boron complexes and clusters

Tanaka

Gon

Ito

et al. 2022

Coordination Chemistry Reviews

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Domino 1,4‐ and 1,4‐Addition Reactions of Ketene Silyl Thioacetals to Dialkynyl Imines Promoted by Scandium Triflate: Synthesis of Multifunctionalized δ‐Lactams

Abstract: Domino 1,4-and 1,4-addition reactions of ketene silyl thioacetals to dialkynyl imines are disclosed. Scandium triflate promoted domino 1,4-and 1,4-addition reactions of ketene silyl thioacetals to dialkynyl imines to give a variety of alkynyl δ-lactams in moderate to good yields.

Cited by 2 publications

References 59 publications

Recent Advances in Scandium(III) Triflate Catalysis: A Review

Recent Advances in Scandium(III) Triflate Catalysis: A Review

Recent progresses in the mechanistic studies of aggregation-induced emission-active boron complexes and clusters

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