Chemodivergent and Stereoselective Access to Fused Isoxazoline Azetidines and Thietanes through [3 + 2]-Cycloadditions

Baumann, Andreas N.; Reiners, Felix; Juli, Thomas; Didier, Dorian

doi:10.1021/acs.orglett.8b02848

Cited by 38 publications

(17 citation statements)

References 38 publications

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“…The regioselectivity of dipolar (3+2)‐cycloadditions is therefore governed by the nature of the group present on the four‐membered ring (either electron‐donating or electron‐withdrawing, Scheme 29). [78] …”

Section: Further Applications Of Unsaturated Four‐membered Ringsmentioning

confidence: 99%

Uncommon Four‐Membered Building Blocks – Cyclobutenes, Azetines and Thietes

Didier

Reiners

2021

The Chemical Record

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Section: Further Applications Of Unsaturated Four‐membered Ringsmentioning

confidence: 99%

Uncommon Four‐Membered Building Blocks – Cyclobutenes, Azetines and Thietes

Didier

Reiners

2021

The Chemical Record

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“…Similarly, if 98 a is used as the azetidine starting material, lithiation followed by electrophilic trapping with B(Oi−Pr) 3 and a Suzuki cross coupling with a vinyl electrophile gives 99 k that can be extracted and treated with N ‐methylsuccinimide to give 104 in a four‐step sequence with a single purification. Fused isoxazoline products have also been prepared using an analogous strategy through the [3+2]‐dipolar cycloaddition of dihydroazetes such as 99 l with nitrile oxides (Scheme C) . The use of 1,2‐dihydroazetes 99 j – 99 l as cycloaddition precursors illustrates the unique azetidine structural diversity that can be accessed via the development of divergent functionalizations of unsaturated azetidines.…”

Section: Development Of Unsaturated Azetidines As Precursors For Divementioning

confidence: 99%

Divergent Functionalizations of Azetidines and Unsaturated Azetidines

Reidl

Anderson

2019

Asian J Org Chem

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Azetidines are unusual heterocyclic motifs that comprise key components of biologically active molecules and provide desirable structural properties for drug discovery. While a variety of methods have been designed for the synthesis of azetidines, screening and optimization studies often require systematic and versatile strategies for varying structural characteristics. With this need in mind, this review surveys methods for the divergent preparation of substituted azetidines from starting materials that contain a 4-membered azacycle. The scope and tolerance of azetidine functionalization reactions are described including approaches such as lithiation and electrophilic trapping, nucleophilic displacement, and transition metal catalysis. To complement this discussion, opportunities for using unsaturated azetidines as precursors to functionalized saturated analogues are also examined as an emerging alternative tactic towards the diversity-oriented preparation of these strained heterocycles. The aim of this Minireview is to identify recent advances, as well as areas where further development is needed, to continue to inspire innovative solutions to the divergent synthesis of functionalized azetidines.[a] T.

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“…For example, thiete sulfones could be used as dienophiles in the Diels–Alder reaction with tetraphenyl cyclopentadienones or isobenzofurans for accessing bridged and fused-ring compounds 20 – 22 . Moreover, they could participate in [3 + 2] cycloadditions with diazo compounds or nitrile oxides for the synthesis of heterocycles 23 , 24 . Recently, thiete sulfones have been investigated in C–H functionalization to establish axially chiral molecules and macrocyclic compounds 25 , 26 .…”

Section: Introductionmentioning

confidence: 99%

Skeletal reorganization divergence of N-sulfonyl ynamides

Zeng

Lin

et al. 2020

Nat Commun

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Skeletal reorganization is a type of intriguing processes because of their interesting mechanism, high atom-economy and synthetic versatility. Herein, we describe an unusual, divergent skeletal reorganization of N-sulfonyl ynamides. Upon treatment with lithium diisopropylamine (LDA), N-sulfonyl ynamides undergo a skeletal reorganization to deliver thiete sulfones, while the additional use of 1,3-dimethyl-tetrahydropyrimidin-2(1H)-one (DMPU) shifts the process to furnish propargyl sulfonamides. This skeletal reorganization divergence features broad substrate scope and scalability. Mechanistically, experimental and computational studies reveal that these processes may initiate from a lithiation/4-exo-dig cyclization cascade, and the following ligand-dependent 1,3-sulfonyl migration or β-elimination would control the chemodivergence. This protocol additionally provides a facile access to a variety of privileged molecules from easily accessible ynamides.

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Chemodivergent and Stereoselective Access to Fused Isoxazoline Azetidines and Thietanes through [3 + 2]-Cycloadditions

Cited by 38 publications

References 38 publications

Uncommon Four‐Membered Building Blocks – Cyclobutenes, Azetines and Thietes

Uncommon Four‐Membered Building Blocks – Cyclobutenes, Azetines and Thietes

Divergent Functionalizations of Azetidines and Unsaturated Azetidines

Skeletal reorganization divergence of N-sulfonyl ynamides

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