Asymmetric synthesis of (+)- or (-)-2-methyloctanal via the metalloenamines of chiral alkoxy amines

Meyers, A. I.; Poindexter, Graham S.; Brich, Zdenek

doi:10.1021/jo00399a021

Cited by 99 publications

(31 citation statements)

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“…The products were purified by column chromatography, and the amino ethers were converted into the hydrochloride salts and recrystallized to give pure 28 and 29, which are known compounds. Their physical data were consistent with the literature, [45] thus supporting that also racemization did not occur during cleavage of the DNs group.…”

Section: Resultssupporting

confidence: 90%

The Dinosyl Group: A Powerful Activator for the Regioselective Alcoholysis of Aziridines

et al. 2011

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Section: Resultssupporting

confidence: 90%

The Dinosyl Group: A Powerful Activator for the Regioselective Alcoholysis of Aziridines

et al. 2011

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“…The general procedure of Pfeffer and Silbert was followed {13) to alkylate the dianion of octanoic acid 1 with methyl iodide producing 2 {92%): b.p. 131-135~ (20 ram) IR,NMR data consistent with assignment (13).…”

Section: Methodssupporting

confidence: 60%

Synthesis and lipase catalyzed hydrolysis of thiolesters of 2‐, 3‐ and 4‐methyl octanoic acids

Sonnet¹,

Baillargeon²

1989

Lipids

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Racemic 2-, 3-and 4-methyloctanoic acids were synthesized. The 2-mercaptoethanol S-esters of these branched acids, and of octanoic acid, were exposed to lipases of the fungi Candida rugosa and Aspergillus niger. Reactions were followed spectrophotometrically using Ellman's Reagent. Branching at the 3-position retards lipolysis more severely than at either the 2-or 4positions. Features of the assay method are discussed with reference to titrimetry.

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“…( S )‐ N ‐Isopropyl‐ O ‐methyl‐valinol : The ( S )‐ N ‐isopropyl‐ O ‐methyl‐valinol was prepared according to published procedures: LiAlH 4 reduction of D ‐valine to D ‐valinol,10 methylation by MeI to afford the amino methyl ether,11 condensation with acetone to the corresponding imine and finally reduction using H 2 /Pd/C in a Parr apparatus at 4 atm 12…”

Section: Methodsmentioning

confidence: 99%

Mixed Dimer and Mixed Trimer Complexes ofnBuLi and a Chiral Lithium Amide

Hilmersson

Malmros

2001

Chem. Eur. J.

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Multinuclear and multidimensional NMR spectroscopy have shown that lithium (S)-N-isopropyl-O-methyl-valinol (1-[6Li]) exists in a mixed 2:1 complex with nBu[6Li], (1-[6Li])2/nBu[6Li], in non-coordinating solvents such as hexane or toluene. A 6Li,1H-HOESY NMR spectrum indicates that the complex is a cyclic trimer with a large distance between the di-coordinated lithium and the carbanion of nBu[6Li]. Such arrangements are present in the solid state as previously reported by Williard and Sun. The exchange of lithium atoms within the trimer is slow at -33 degrees C. The exchange barrier (deltaG++) was determined to be 14.7 kcal x mol(-1) from quantitative 6Li,6Li-EXSY spectra. Addition of diethyl ether results in the formation of mixed dimers of (1-[6Li])/nBu[6Li], tetramers of nBu[6Li], and homodimers (1-[6Li])2. The apparent equilibrium constant of the mixed dimer was determined from the 6Li NMR integrals as K = 7.

show abstract

Asymmetric synthesis of (+)- or (-)-2-methyloctanal via the metalloenamines of chiral alkoxy amines

Cited by 99 publications

References 1 publication

The Dinosyl Group: A Powerful Activator for the Regioselective Alcoholysis of Aziridines

The Dinosyl Group: A Powerful Activator for the Regioselective Alcoholysis of Aziridines

Synthesis and lipase catalyzed hydrolysis of thiolesters of 2‐, 3‐ and 4‐methyl octanoic acids

Mixed Dimer and Mixed Trimer Complexes ofnBuLi and a Chiral Lithium Amide

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