Nonracemic menthyl phosphorylacetates

Бредихин, А. А.; Елисеенкова, Р. М.; Tarasova, R. I.; Voskresenskaya, O. V.; Баландина, А. А.; Dobrynin, A. B.; Latypov, Shamil K.; Литвинов, И. А.; Шарафутдинова, Д. Р.; Efremov, Yu. Ya.

doi:10.1007/s11172-007-0047-7

Cited by 3 publications

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References 10 publications

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“…However, the phosphonite borane (BH 3 )PPh(OMen) 2 ( 1 ) and the phosphine borane (BH 3 )PPh(dbf) 2 ( 2 ) were isolated as the major products of the reaction as white solids. The parent phosphines of 1 and 2 , (OMen) 2 PPh and (dbf) 2 PPh, have both been previously reported, though to the best of our knowledge 1 and 2 are new compounds. As expected, the 31 P{ 1 H} NMR resonance for compound 1 is much further downfield than 2 ( 1 : δ 129.50; 2 : δ 12.60).…”

Section: Resultsmentioning

confidence: 84%

Toward Stereoselective Lactide Polymerization Catalysts: Cationic Zinc Complexes Supported by a Chiral Phosphinimine Scaffold

2011

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The P-stereogenic phosphinimine ligands (dbf)MePhP═NAr (7: Ar = Dipp; 8: Ar = Mes; dbf = dibenzofuran, Dipp = 2,6-diisopropylphenyl, Mes = 2,4,6-trimethylphenyl) were synthesized as racemates via reactions of the parent phosphines (rac)-(dbf)MePhP (6) with organoazides. The ligands 7 and 8 were protonated by Brønsted acids to afford the aminophosphonium borate salts [(7)-H][BAr(4)] (9: Ar = C(6)F(5); 11: Ar = Ph) and [(8)-H][BAr(4)] (10: Ar = C(6)F(5); 12: Ar = Ph). The protonated ligands 9 and 10 were active toward alkane elimination reactions with diethylzinc and ethyl-[methyl-(S)-lactate]zinc to give the heteroleptic complexes [{(dbf)MePhP═NAr}ZnR][B(C(6)F(5))(4)] (Ar = Dipp, 13: R = Et; 15: R = methyl-(S)-lactate; Ar = Mes, 14: R = Et; 16: R = methyl-(S)-lactate). By contrast, reaction of the tetraphenylborate derivative 11 with diethylzinc yielded a phenyl transfer product, [(dbf)MePhP═NDipp]ZnPh(2) (17). Complex 15 was found to catalyze the ring-opening polymerization of rac-lactide.

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Section: Resultsmentioning

confidence: 84%

Toward Stereoselective Lactide Polymerization Catalysts: Cationic Zinc Complexes Supported by a Chiral Phosphinimine Scaffold

2011

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Nonracemic Menthyl Phosphorylacetates

et al. 2007

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Non-Selective Reduction of P-Stereogenic Phosphinoylacetic Acid Esters and 3-Phosphorylated Coumarins to Phosphino-Boranes: Discovery of Unexpected 2,3-Dihydrobenzofuran Derivative

Dziuba,

Walczak,

Szwaczko

2024

Symmetry

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This paper presents the efficient reduction of phosphinoylacetic acid esters and 3-phosphorylated coumarin to their corresponding phosphino-boranes using BH₃-THF complexes. Optimized conditions for the reduction of phosphinoylacetic acid esters resulted in high yields of phosphinoborates. The straightforwardness and efficiency of the process were demonstrated for diarylphosphinoylacetic acid ethyl esters, as well as P-stereogenic L-menthyl esters, where the simultaneous reduction of the strong P=O bond and the ester group was exclusively observed for the first time. The study also highlighted the significant influence of steric effects with bulky substituents, such as the menthol group or the 1-naphthyl substituent at phosphorus, on the reduction efficiency. However, the reduction of 3-phosphorylated coumarins produced an unexpected reaction product: a 2,3-dihydrobenzofuran derivative. The present findings provide valuable information on the direct reduction of phosphine oxides and related compounds, demonstrating the versatility of borane complexes in synthetic chemistry, and provide new perspectives for studying the problems of symmetry and asymmetry in the chemistry of such transformations.

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Nonracemic menthyl phosphorylacetates

Cited by 3 publications

References 10 publications

Toward Stereoselective Lactide Polymerization Catalysts: Cationic Zinc Complexes Supported by a Chiral Phosphinimine Scaffold

Toward Stereoselective Lactide Polymerization Catalysts: Cationic Zinc Complexes Supported by a Chiral Phosphinimine Scaffold

Nonracemic Menthyl Phosphorylacetates

Non-Selective Reduction of P-Stereogenic Phosphinoylacetic Acid Esters and 3-Phosphorylated Coumarins to Phosphino-Boranes: Discovery of Unexpected 2,3-Dihydrobenzofuran Derivative

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