A facile synthesis of homochiral 1-norbornanecarboxylic acids and 1-norbornanecarbonitriles

Martı́nez, Antonio Garcı́a; Vilar, Enrique Teso; Fraile, Amelia Garcı́a; Cerero, Santiago de la Moya; Diego, J. M. Gonzalez‐Fleitas De; Subramanian, L. R.

doi:10.1016/0957-4166(94)80130-4

Cited by 10 publications

(1 citation statement)

References 19 publications

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“…The enantiospecific synthesis of 1a and 1b , starting from (1 R )‐fenchone and (1 R )‐camphor respectively, has been previously reported by us 39. Epoxidation of 1 with m ‐CPBA yields a mixture of spiroepoxides 2 and 3 with 40% d.e.…”

Section: Resultsmentioning

confidence: 79%

The role of the C(2) configuration and methyl substitution on the catalytic activity of novel 2,3,3‐ and 2,7,7‐trimethyl‐substituted γ‐aminonorbornan‐2‐ols

Martı́nez¹,

Vilar

Fraile

et al. 2010

Chirality

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A new set of optically active 2,3,3- and 2,7,7-trimethyl-substituted gamma-aminonorbornan-2-ols have been obtained from 2-methylenenorbornane-1-carbonitriles derived from (+)-camphor and (-)-fenchone and probed as chiral ligands for the enantioselective addition of diethylzinc to benzaldehyde. This has allowed the study of the structural factors influencing the chirality transfer, such as variation of the relative configuration at C(2) and steric hindrance at C(2), C(3), and C(7) positions of norbornane, which result in the observance of the important role played by the gem-dimethyl position in gamma-aminonorbornan-2-exo-ols. An empirical rationalization of the obtained experimental results has been realized on the basis of energetically-favored diastereomeric Noyori-like transition states.

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Section: Resultsmentioning

confidence: 79%

The role of the C(2) configuration and methyl substitution on the catalytic activity of novel 2,3,3‐ and 2,7,7‐trimethyl‐substituted γ‐aminonorbornan‐2‐ols

Martı́nez¹,

Vilar

Fraile

et al. 2010

Chirality

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ChemInform Abstract: A Facile Synthesis of Homochiral 1‐Norbornanecarboxylic Acids and 1‐ Norbornanecarbonitriles.

et al. 1995

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Electron ionization mass spectral studies of bridgehead‐substituted norbornan‐2‐ones: camphor derivatives

Vilar

Fraile

Cerero

et al. 2011

Rapid Comm Mass Spectrometry

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The electron ionization (EI) mass spectra of a series of bridgehead-substituted 3,3-dimethylnorbornan-2-ones, derived from natural (1R)-(+)-camphor, have been studied and their cleavage mechanisms rationalized on the basis of the substituent shifts as well as on the identification of relevant peaks through accurate mass measurements and collision-induced dissociation (CID) tandem mass spectrometric experiments. The fragmentation patterns are very dependent on both the structural nature and the electronic properties of the bridgehead substituent. The driving force for the main fragmentation pathways are competitive cleavages of the C(1)-C(2) and C(2)-C(3) bonds directed by the bridgehead substituent and either the gem-dimethyl or carbonyl groups. These cleavages lead to distonic ions in which the charge is preferentially located either at the C(1), C(2) or C(3) positions depending on the electronic character and structural nature of the bridgehead substituent. This charge distribution determines the subsequent rearrangements and fragmentations.

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A facile synthesis of homochiral 1-norbornanecarboxylic acids and 1-norbornanecarbonitriles

Cited by 10 publications

References 19 publications

The role of the C(2) configuration and methyl substitution on the catalytic activity of novel 2,3,3‐ and 2,7,7‐trimethyl‐substituted γ‐aminonorbornan‐2‐ols

The role of the C(2) configuration and methyl substitution on the catalytic activity of novel 2,3,3‐ and 2,7,7‐trimethyl‐substituted γ‐aminonorbornan‐2‐ols

ChemInform Abstract: A Facile Synthesis of Homochiral 1‐Norbornanecarboxylic Acids and 1‐ Norbornanecarbonitriles.

Electron ionization mass spectral studies of bridgehead‐substituted norbornan‐2‐ones: camphor derivatives

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