2012
DOI: 10.1002/anie.201203911
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Concise Synthesis of Acetal‐Protected syn 1,3‐Diols by a Tandem Hemiacetal Formation/Tsuji–Trost Reaction

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Cited by 42 publications
(8 citation statements)
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References 58 publications
(17 reference statements)
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“…Menche and Wang 52 reported the first approach using one of these strategies in 2012. They used a palladium catalyst and acetaldehyde to generate the hemiacetal, and used carbonates as leaving groups (Scheme 23).…”
Section: Scheme 22mentioning
confidence: 99%
“…Menche and Wang 52 reported the first approach using one of these strategies in 2012. They used a palladium catalyst and acetaldehyde to generate the hemiacetal, and used carbonates as leaving groups (Scheme 23).…”
Section: Scheme 22mentioning
confidence: 99%
“…In 2012, Wang and Menche reported the use of acetaldehyde as tether for the synthesis of syn 1,3-diols via tandem hemiacetal formation and Tsuji–Trost reaction with a simple palladium catalyst ( Scheme 2 ). 13 This 3-step relay process involved (i) hemiacetal formation from a chiral homoallylic alcohols and acetaldehyde, (ii) palladium π-allyl complex formation, and (iii) intramolecular allylic substitution.…”
Section: Tethers For Regioselective Tsuji–trost Reactionsmentioning
confidence: 99%
“…10m-p,17 The realization of this concept is depicted in Scheme 6. 18 The most effective conditions for the selective synthesis of syn-1,3dioxanes of type 16 relied on homoallylic alcohol 10 in acetaldehyde as a co-solvent, with a slight excess of KHMDS (1.5 eq.) and catalytic amounts of [Pd(allyl)Cl] 2 (10%) and PPh 3 (30%) at room temperature, in toluene.…”
Section: Tandem Synthesis Of Acetal-protected 13-diolsmentioning
confidence: 99%
“…Importantly, the generated terminal alkene functionality may serve as a synthetic handle for the further elaboration of the target, as demonstrated in a fragment synthesis of macrolide RK-397 (not shown). 18…”
Section: Tandem Synthesis Of Acetal-protected 13-diolsmentioning
confidence: 99%