Synthetic Applications of Dealkoxycarbonylations of Malonate Esters, β-Keto Esters, α-Cyano Esters and Related Compounds in Dipolar Aprotic Media - Part I

Krapcho, A. Paul

doi:10.1055/s-1982-29953

Cited by 415 publications

(183 citation statements)

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“…Next, we attempted to obtain 5a from 14 using acidic conditions. 12 This provided racemic 5a,5b, which after reduction with sodium borohydride yielded a mixture of stereoisomers, viz., 1a, 1b and 2a, 2b, respectively (Scheme 2). Each enantiomeric pair was separated by liquid chromatography over silica gel in the ratio of 2.1:1.0 (1a,1b:2a,2b); the fast moving spot 2a,2b crystallized and its X-ray analysis showed them as a racemic mixture consisting of enantiomers (2S,2´S) 2a and its mirror image (2R,2´R) 2b.…”

Section: Resultsmentioning

confidence: 99%

An easy access to two epimeric N-substituted (2S)-2-(2'-hydroxypropyl)pyrrolidines

Silva

Cottier

Srivastava

et al. 2005

J. Braz. Chem. Soc.

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Uma fácil e eficiente síntese para obtenção de β-aminocetonas 5a, 6 e γ-aminoálcoois 1a, 2a, 3, 4 enantiomericamente puros a partir de L-prolinol 7 e L-prolina 15 é descrita. A etapa principal da reação foi o uso do reagente de Tebbe que permitiu a transformação da função éster a um enol éter que após hidrólise formou a cetona sem nenhuma racemização.An easy and efficient route for the synthesis of enantiomerically pure β-aminoketones 5a, 6 and γ-aminoalcohols 1a, 2a, 3, 4 from L-prolinol 7 and L-proline 15 is described. One of the key steps is the use of Tebbe´s reagent allowing the transformation of the ester function to an enol ether without any racemization.

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Section: Resultsmentioning

confidence: 99%

An easy access to two epimeric N-substituted (2S)-2-(2'-hydroxypropyl)pyrrolidines

Silva

Cottier

Srivastava

et al. 2005

J. Braz. Chem. Soc.

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“…We also found that basic hydrolysis followed by acidification and decarboxylation were in some cases more efficient (see experimental part). Krapcho described the dealkoxycarbonylation of β-keto esters in wet DMSO, containing sodium chloride 10 .…”

Section: Figurementioning

confidence: 99%

Efficient synthesis of 2-alkyl-2-hydroxy-6-X-1-tetralones

Pažický¹,

Semak²,

Gášpár³

et al. 2008

Arkivoc

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“…1,1,6,6-tetracarboxylate according to Krapcho (1982), obtained colorless crystals (m.p. 342-343 K) from DMSO, and measured density by suspension in aqueous solutions of Zn(NO3)2.…”

Section: Experimental M Choubal Prepared the Title Compound (I) Fromentioning

confidence: 99%

Structure of diethyl cis,cis-3,8-cyclodecadiene-trans-1,6-dicarboxylate

Choubal¹,

Fernandez²,

Crumrine³

et al. 1992

Acta Crystallogr C

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Abstract. C16H2404, M r : 280.36, triclinic, P1, a = 6.5675 (8), b = 11.9949 (14), c = 5.1052 (6) ,~, a = 93.418 (4), fl = 100.420 (4), y = 74.612 (6) Two sets of intensity measurements were made using a modified Picker FACS-I diffractometer in the 0-20 scan mode over the range -50 < 20 < 50 °, maximum sin0/A = 0.595 ,~-~. A total of 5448 reflections were encountered between the h, k, l limits of _+ 7, _+ 14 and 0----6, respectively. Five standard reflections (161, 13,~, 312, 132 and 331) measured after every 150 showed less than 2% intensity change so corrections for crystal decay were not applied. Empirical absorption corrections were applied based on intensity variations of three reflections measured at regular intervals in ~o with X--90°. Transmission factors ranged from 1.00 to 0.92. Intensity data were merged for symmetry equivalents to yield 1340 unique reflections (Rint = 0.049) and converted to

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Synthetic Applications of Dealkoxycarbonylations of Malonate Esters, β-Keto Esters, α-Cyano Esters and Related Compounds in Dipolar Aprotic Media - Part I

Cited by 415 publications

References 0 publications

An easy access to two epimeric N-substituted (2S)-2-(2'-hydroxypropyl)pyrrolidines

An easy access to two epimeric N-substituted (2S)-2-(2'-hydroxypropyl)pyrrolidines

Efficient synthesis of 2-alkyl-2-hydroxy-6-X-1-tetralones

Structure of diethyl cis,cis-3,8-cyclodecadiene-trans-1,6-dicarboxylate

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