Crotylation of Aldehydes by Crotyltins: Discrimination between Mechanisms Involving Transmetallation or Simple Lewis Acid Assistance through the Consideration of the Stereochemistry of the Corresponding Homoallylic Alcohols

Fargeas, Valérie; Zammattio, Françoise; Chrétien, Jacques R.; Bertrand, Marie‐Jo; Paris, Michaël; Quintard, Jean‐Paul

doi:10.1002/ejoc.200701183

Cited by 17 publications

(8 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…(5)]. Interestingly, the α‐addition product 3 ai was obtained as the Z ‐isomer [13] and 3 ae was formed as 1.4 : 1 mixture of inseparable diastereomers.…”

Section: Resultsmentioning

confidence: 99%

Gold(I)‐Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates

et al. 2022

View full text Add to dashboard Cite

Gold(I)-catalyzed nucleophilic allylations of pyridinium and quinolinium ions with various allyl pinacolboronates are reported. The reactions are completely selective with respect to the site of the azinium ion that is attacked, to give various functionalized 1,4dihydropyridines and 1,4-dihydroquinolines. Evidence suggests that the reactions proceed through nucleophilic allylgold(I) intermediates formed by transmetalation from allylboronates. Density functional theory (DFT) calculations provided mechanistic insight.

show abstract

“…(5)]. Interestingly, the α‐addition product 3 ai was obtained as the Z ‐isomer [13] and 3 ae was formed as 1.4 : 1 mixture of inseparable diastereomers.…”

Section: Resultsmentioning

confidence: 99%

Gold(I)‐Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates

et al. 2022

View full text Add to dashboard Cite

show abstract

“…With supported crotyltins we have already observed a slower 1,3-metallotropy when compared to crotyltributyltin [25], and in the case of a-substituted c-ethoxyallyltins, their poor ability to give a 1,3-metallotropy due to the stabilization occurring in the Z-isomer, possibly because of coordination expansion of the tin atom by an oxygen one, results in a regioselective reaction affording the mono-protected a-glycols. Comparison of the reaction using the supported allyltin with its analogue in solution reveals that the diastereoselectivity remains nearly unaffected.…”

Section: Assessment Of the Reactivity Of The Supported Vinyltins And mentioning

confidence: 92%

“…Differences in reactivity of supported crotyltins toward benzaldehyde were observed when compared to crotyltributyltin, due to a matrix effect on the kinetics of 1,3-metallotropy [25]. HRMAS NMR techniques enable one to estimate semi-quantitatively the differences in isomeric composition of the supported reagents as a function of their preparation method.…”

Section: Supported Crotyltinsmentioning

confidence: 96%

Synthesis, characterization and primary evaluation of the synthetic efficiency of supported vinyltins and allyltins

Kerric

Grognec

Fargeas

et al. 2010

Journal of Organometallic Chemistry

Self Cite

View full text Add to dashboard Cite

“…We considered the halogenation reaction of aromatic amines [41], the allylation reaction of aldehydes [42][43][44], and the Stille cross-coupling reaction of vinyltins with arylhalides [45]. The efficiency of the immobilized reagents was illustrated by a similar reactivity when compared to their soluble 0022-328X/$ -see front matter Ó 2009 Elsevier B.V. All rights reserved.…”

Section: Introductionmentioning

confidence: 99%