Propargylation of Aldehydes Using Potassium Allenyltrifluoroborate

Couto, Túlio R.; Freitas, Jucleiton José Rufino de; Freitas, Juliano Carlo Rufino; Cavalcanti, Italo H.; Menezes, Paulo H.; Oliveira, Roberta A.

doi:10.1055/s-0034-1379163

Cited by 4 publications

(1 citation statement)

References 10 publications

(15 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Although the desired products 2a-t having been obtained along with a small proportion of the corresponding regioisomer in some cases, in the development of new synthetic methods, it is desirable that it gives the corresponding product as a single compound. Our group described the synthesis of homopropargylic alcohols using potassium allenyltrifluoroborate as the propargylating agent in a very regioselective way [36,37]. Thus, allenylboronic acid pinacol ester (1) was converted into the corresponding trifluoroborate using the procedure described by Lloyd-Jones and co-worker [38].…”

Section: Resultsmentioning

confidence: 99%

Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation

Freitas¹,

Freitas²,

Andrade³

et al. 2020

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation

Freitas¹,

Freitas²,

Andrade³

et al. 2020

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: Propargylation of Aldehydes Using Potassium Allenyltrifluoroborate.

Couto

Freitas

et al. 2015

ChemInform

View full text Add to dashboard Cite

Propargylation of Aldehydes Using Potassium Allenyltrifluoroborate. -A novel protocol for the fast and simple propargylation of aldehydes with potassium allenyltrifluoroborate furnishes products in high yields and purity. The reaction proceeds under mild conditions in a regio-and chemoselective manner. Commercially available Amberlyst 31 sulfonic acid resin is efficiently used as catalyst. -(COUTO, T. R.; FREITAS, J. J. R.; FREITAS, J. C. R.; CAVALCANTI, I. H.; MENEZES, P. H.; OLIVEIRA*, R. A.; Synthesis 47 (2015) 1, 71-78, http://dx.doi.org/10.1055/s-0034-1379163 ; Dep. Quim. Fundam., Univ. Fed. Pernambuco, 50740 Recife, Pernambuco, Brazil; Eng.) -B. Bergmann 23-073

show abstract

Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives

et al. 2018

View full text Add to dashboard Cite

A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated by providing access to known fungal decanolides as well as novel aromatic macrocycles. The protocol provided a gram-scale route to (-)-aspinolide A and (-)-5-epi-aspinolide A utilizing a catalytic Nozaki-Hiyama-Kishi reaction to close the macrolide in the final step in 65-84% yields.

show abstract

Propargylation of Aldehydes Using Potassium Allenyltrifluoroborate

Cited by 4 publications

References 10 publications

Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation

Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation

ChemInform Abstract: Propargylation of Aldehydes Using Potassium Allenyltrifluoroborate.

Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives

Contact Info

Product

Resources

About