Chemoselective oxidative hydrolysis of EWG protected α-arylamino vinyl bromides to α-arylamino-α′-bromoacetones

Pace, Vittorio; Castoldi, Laura; Hernáiz, María J.; Alcántara, Andrés R.; Hölzer, W.

doi:10.1016/j.tetlet.2013.05.118

Cited by 9 publications

(2 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…N -(2-Bromoallyl)- N -phenylacetamide, isolated by flash column chromatography (petroleum ether/ethyl acetate = 16:1) in 42% yield (1601 mg), pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ) δ = 1.91 (s, 3H), 4.60 (s, 2H), 5.51 (s, 1H), 5.65 (s, 1H), 7.24–7.27 (m, 2H), 7.34–7.44 (m, 3H); 13 C{ 1 H} NMR (100 MHz, CDCl 3 ) δ = 170.5, 142.2, 129.7, 128.6, 128.2, 128.0, 119.5, 56.3, 22.7; HRMS (ESI-TOF) calcd for C 11 H 13 BrNO + ([M + H] + ) 254.0175.…”

Section: Experimental Sectionmentioning

confidence: 99%

Benzylarylation of N-Allyl Anilines: Synthesis of Benzylated Indolines

Huang

Song

et al. 2019

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

Section: Experimental Sectionmentioning

confidence: 99%

Benzylarylation of N-Allyl Anilines: Synthesis of Benzylated Indolines

Huang

Song

et al. 2019

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…[18] In this sense, a general method has been developed by Pace et al who employed Weinreb amides [19] 13 as the electrophilic starting materials (Scheme 4b, c). [10,20] Remarkably, the use of such amides could be successfully extended to the synthesis of a 0 -halo-a,b-unsaturated ketones 16, for which the use of esters provided exclusively the double-addition products (i.e. carbinols).…”

Section: Homologation Of Carboxylic Acid Derivativesmentioning

confidence: 99%

Halomethyllithium Carbenoids: Versatile Reagents for the Homologation of Electrophilic Carbon Units

Pace¹

2014

Aust. J. Chem.

Self Cite

View full text Add to dashboard Cite

A New Approach to Models of the 4,5‐Dihydroxycyclopentenone Core of the Kodaistatins A–D: Elucidation of the Diol Configuration in Kodaistatin A

Peter

Brückner

2017

Chemistry A European J

View full text Add to dashboard Cite

Abstract:The kodaistatins A-D are strongly anti-diabetic natural products from Aspergillus terreus that hold some promise of an ovel diabetes cure. However,c onsiderations of that kindf ace two drawbacks: 1) The kodaistatins A-D contain ah eavily substituted pulvinone/cyclopentenone combination;2 )they are 1,2-diols, the 3D structures of which have not been assigned yet. However,w ec an exclude two of the four possible stereostructures. We conclude that kodaistatin Ai satrans-, not a cis-diol from NMR comparisons with ap air of cis, trans-isomerick odaistatin models, which we synthesized in 11 and 12 steps, respectively.T he stereocenters of the diol moiety arosefrom stereocomplementary,h ighly diastereoselective aldol additions of al ithium enolate or the corresponding silyl ketene acetal. The cyclopentenone moieties stemmed from intramolecular aldol additions and ensuingd ehydrations. The requisite enolates wereo btained by the reduction of a-bromoketones with samarium diiodide.

show abstract

Chemoselective oxidative hydrolysis of EWG protected α-arylamino vinyl bromides to α-arylamino-α′-bromoacetones

Cited by 9 publications

References 30 publications

Benzylarylation of N-Allyl Anilines: Synthesis of Benzylated Indolines

Benzylarylation of N-Allyl Anilines: Synthesis of Benzylated Indolines

Halomethyllithium Carbenoids: Versatile Reagents for the Homologation of Electrophilic Carbon Units

A New Approach to Models of the 4,5‐Dihydroxycyclopentenone Core of the Kodaistatins A–D: Elucidation of the Diol Configuration in Kodaistatin A

Contact Info

Product

Resources

About