Palladium-Catalyzed Highly Enantioselective Cycloaddition of Vinyl Cyclopropanes with Imines

Huang, Xiaobing; Li, Xian-Jing; Li, Tiantian; Chen, Bin; Chu, Wen‐Dao; He, Long; Liu, Quan-Zhong

doi:10.1021/acs.orglett.9b00274

Cited by 59 publications

(22 citation statements)

References 40 publications

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“…202 Chu, He and Liu have recently reported an enantioselective cycloaddition of vinyl cyclopropanes with isatin derived imines using ligand 42, to form 3,2′-spiro-derivatives (Scheme 42). 203 MBH carbonates. As seen throughout this review, the use of isatin derived MBH carbonates is significant to form a 1,3dipole as a three carbon synthon.…”

Section: [3 + 2]-cycloadditionmentioning

confidence: 99%

Stereoselective synthesis and applications of spirocyclic oxindoles

2021

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Section: [3 + 2]-cycloadditionmentioning

confidence: 99%

Stereoselective synthesis and applications of spirocyclic oxindoles

2021

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“…In this reaction, the diastereoselectivity was improved by the addition of LiCl (Scheme 22 c). [37b] The dipolarophiles were also extended to aldimines and isatin‐derived ketimines, affording enantioenriched pyrrolidine and spiro[pyrrolidin‐3,2′‐oxindole] derivatives, respectively [37c] …”

Section: Asymmetric Reactions Of Vinyl‐substituted Cyclopropanesmentioning

confidence: 99%

Asymmetric Catalytic Reactions of Donor–Acceptor Cyclopropanes

2020

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Due to the synergistic “push–pull” effect of vicinal electron‐donating and electron‐withdrawing groups, donor–acceptor (D‐A) cyclopropanes have been recognized as one of the most powerful building blocks to generate polyfunctional reactive intermediates after a strain‐driven ring cleavage. Enantioselective reactions of D‐A cyclopropanes provide an efficient approach to enantioenriched acyclic and cyclic compounds. A number of chiral Lewis/Brønsted acids, transition metals, and organocatalysts have been designed for such transformations, including ring‐openings, annulations, and rearrangements. This minireview highlights the developments and new advances in this field and describes new synthetic opportunities offered by these interesting methodologies.

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“…Liu et al. have devised a palladium‐catalyzed asymmetric formal [3+2] cycloaddition reaction of VCPs 27 with aldimines 92 or isatin‐derived ketimines 91 in the presence of chiral phosphoramidite ligands ( L 2 and L 3 ) and realized the construction of the corresponding highly functionalized and optically enriched pyrrolidine 94 or spiro[pyrrolidin‐3,2‐oxindole] 93 derivatives in up to 94% yield along with up to 96% ee and 7:1 dr (Scheme ) . Isatin‐derived ketimines having a benzyl group as N‐substituent provided better selectivity as compared to other substituents like methyl, acetyl, and methoxymethyl, providing the major isomer with 92% ee and 4:1 dr .…”

Section: Synthesis Of Five‐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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Palladium-Catalyzed Highly Enantioselective Cycloaddition of Vinyl Cyclopropanes with Imines

Cited by 59 publications

References 40 publications

Stereoselective synthesis and applications of spirocyclic oxindoles

Stereoselective synthesis and applications of spirocyclic oxindoles

Asymmetric Catalytic Reactions of Donor–Acceptor Cyclopropanes

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

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