2018
DOI: 10.1021/acs.joc.7b02786
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Regiodivergent Stereoselective Access to Fused Alkylideneazetidines

Abstract: Following recent advances in the generalization and simplification of 2H-azetine synthesis, a regiodivergent approach to fused 2- and 3-alkylideneazetines was designed via the intermediate formation of unprecedented vinylazetine structures. Concise sequences to the latter are described from which an expected unsaturated fused ring system was isolated with very high yields and regio- and stereoselectivities by [4 + 2] cycloadditions.

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Cited by 22 publications
(16 citation statements)
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“…Diels‐Alder cycloadditions using these compounds led to two different fused alkylideneazetidine regioisomers. Products containing up to five stereocenters were isolated in great yields and excellent dr. An endo model can be proposed to account for the observed stereochemical outcome, as depicted in Scheme 28 [76] …”
Section: Further Applications Of Unsaturated Four‐membered Ringsmentioning
confidence: 99%
“…Diels‐Alder cycloadditions using these compounds led to two different fused alkylideneazetidine regioisomers. Products containing up to five stereocenters were isolated in great yields and excellent dr. An endo model can be proposed to account for the observed stereochemical outcome, as depicted in Scheme 28 [76] …”
Section: Further Applications Of Unsaturated Four‐membered Ringsmentioning
confidence: 99%
“…Surprisingly, when racemic 99 i was subjected to hydrogenation conditions, secondary interactions with the Pd/C catalyst resulted in diastereoselective formation of 102 . Beyond reduction, Didier and coworkers have also used their sequential elimination, lithiation, and Suzuki cross coupling process to access 1,2‐dihydroazete dienes for cycloaddition processes . As shown in Scheme A, when 3‐vinyl azetidine 98 c , is processed through the lithiation and electrophilic trapping sequence with Me 3 SiCl and 99 j is isolated as a crude product, this compound can be further treated with N ‐methylsuccinimide to give cycloaddition product 103 in a three‐step sequence prior to a single purification.…”
Section: Development Of Unsaturated Azetidines As Precursors For Divementioning
confidence: 99%
“…Following our recent advances on the synthesis of four-membered carbo- and heterocycles, we set out to investigate the formation of non-natural substituted amino acids through a simple stereocontrolled sequence involving the intermediate formation of unsaturated prochiral azetinyl-carboxylic acids. We envisioned that further asymmetric hydrogenation would furnish the desired functionalized azetidine carboxylic acid compounds diastereo- and enantioselectively (Scheme C) .…”
mentioning
confidence: 99%