Ring‐Opening 1‐Amino‐3‐aminomethylation of Donor–Acceptor Cyclopropanes via 1,3‐Diazepanes

Garve, Lennart K. B.; Jones, Peter G.; Werz, Daniel B.

doi:10.1002/anie.201704619

Cited by 159 publications

(39 citation statements)

References 88 publications

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“…In 2017, the Werz group reported a formal [4+3]-cycloaddition reaction between donor-acceptor cyclopropanes 64 and 1,3,5-triazinanes using Sc(OTf) 3 as Lewis acid (Scheme 29b). 33 This mild reaction enabled synthesis of diversely functionalized 1,3-diazepanes 65 with generally high yields. Competition experiment results suggest that 1,3,5-triazinanes directly participate in the reaction rather than being decomposed into three formaldimine molecules.…”

Section: Short Review Syn Thesismentioning

confidence: 98%

Recent Advances of 1,3,5-Triazinanes in Aminomethylation and Cycloaddition Reactions

Liang¹,

Xiao²,

Chen³

2020

Synthesis

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1,3,5-Trisubstituted 1,3,5-triazinanes (hexahydro-1,3,5-triazines), as stable and readily available surrogates for formaldimines, have found extensive applications for the construction of various nitrogen-containing compounds. The formaldimines, formed in situ from this reagent class, can participate in various aminomethylation and cycloaddition reactions. This short review presents recent advances in this field with emphasis on the conceptual ideas behind the developed methodologies and the reaction mechanisms.1 Introduction2 Aminomethylations with 1,3,5-Triazinanes3 Cycloadditions with 1,3,5-Triazinanes3.1 Use of 1,3,5-Triazinanes as Two-Atom Synthons3.2 Use of 1,3,5-Triazinanes as Three-Atom Synthons3.3 Use of 1,3,5-Triazinanes as Four-Atom Synthons3.4 Use of 1,3,5-Triazinanes as Six-Atom Synthons4 Conclusions

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Section: Short Review Syn Thesismentioning

confidence: 98%

Recent Advances of 1,3,5-Triazinanes in Aminomethylation and Cycloaddition Reactions

Liang¹,

Xiao²,

Chen³

2020

Synthesis

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“…developed an efficient approach for the ring opening of DACs to give diamine 150 . The 1,3‐bisfunctionalization was obtained using cyclopropane 3 , triazinanes 4 , and Sc(OTf) 3 as a catalyst, followed by treatment with acid (Scheme ) . In this transformation, seven‐membered 1,3‐diazepanes 149 were formed through formal [4+3] cycloaddition reaction of DAC 3 and traiazinanes 4 in the presence of Sc(OTf) 3 .…”

Section: Synthesis Of Seven‐ and Eight‐membered Nitrogen Heterocyclesmentioning

confidence: 99%

Donor–Acceptor Cyclopropanes as an Expedient Building Block Towards the Construction of Nitrogen‐Containing Molecules: An Update

et al. 2020

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Nitrogen‐containing molecules are the key structural constituent of many pharmaceutical compounds that play a pivotal role in drug development. Owing to their multifaceted medicinal importance, several synthetic approaches have been delineated in the recent past for their construction. Over the past few decades the augmented use of donor–acceptor cyclopropanes (DACs) as three‐carbon synthetic equivalents, despite their ring strain, for the construction of innumerable hetero‐ and carbocycles of pharmaceutical importance has raised the interest of synthetic chemists to this topic. Owing to their zwitterionic nature due to the vicinal disposition of donor and acceptor groups, they have been frequently used in ring‐opening reactions, cycloadditions, and rearrangements. This review is mainly focused on assorted reactions of DACs with various nitrogen‐containing dipolarophiles like imines, azides, cyanates, isothiocyanates, nitrosocarbonyls, hydrazines, diaziridines, triazinanes, diazenes, etc. towards the synthesis of nitrogen‐containing molecules of pharmaceutical and industrial importance. This review is in continuation of our review published in the Israel Journal of Chemistry in April 2016, and includes the literature from April 2016 to May 2019.

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“…[6][7][8][9] However, due to the limited number of examples using Sc, Fe, or Zn, these examples will not be discussed in the scope of this paper. [10][11][12] The (4+3)-cycloaddition involves a three-atom synthon with a four-atom synthon (Figure 1.1). These synthons can be all-carbon moieties (i.e., a diene) or include heteroatoms (i.e., an azomethine).…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Transition-Metal-Catalyzed (4+3)-Cycloadditions

Lam

Lautens²

2020

Synthesis

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A (4+3)-cycloaddition combines a four-atom synthon and three-atom synthon to form seven-membered rings. In the past decade, many improvements have been made to this class of cycloaddition, including excellent diastereo- and enantioselectivities, both intra- and intermolecularly. Through the strategic use of transition-metal catalysts, acids, bases, and organocatalysts, it is possible to perform the cycloaddition on a variety of substrates, generating novel seven-membered rings. With these advances, (4+3)-cycloaddition has also been applied to the synthesis of biologically relevant compounds and natural products. We exclude the cycloadditions of cyclic dienes such as furan, pyrrole, cyclohexadiene or cyclopentadiene as Chiu, Harmata, Mascareñas and others have recently published thorough reviews on that topic. We will however discuss the recent additions (2009–2020) to the literature for the (4+3)-cycloadditions involving other types of four-atom synthons.1 Introduction2 Rhodium2.1 Cyclopropanation/Cope Rearrangement2.2 C–H activation3 Gold, Silver4 Copper5 Palladium, Platinum, Iridium6 Dual-Activation7 Conclusion

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Ring‐Opening 1‐Amino‐3‐aminomethylation of Donor–Acceptor Cyclopropanes via 1,3‐Diazepanes

Cited by 159 publications

References 88 publications

Recent Advances of 1,3,5-Triazinanes in Aminomethylation and Cycloaddition Reactions

Recent Advances of 1,3,5-Triazinanes in Aminomethylation and Cycloaddition Reactions

Donor–Acceptor Cyclopropanes as an Expedient Building Block Towards the Construction of Nitrogen‐Containing Molecules: An Update

Recent Advances in Transition-Metal-Catalyzed (4+3)-Cycloadditions

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