Absolute configuration of conhydrine

1969 ◽  
Vol 47 (23) ◽  
pp. 4393-4397 ◽  
Author(s):  
G. Fodor ◽  
E. Bauerschmidt ◽  
J. Cymerman Craig
Keyword(s):  
Absolute Configuration ◽  
Catalytic Hydrogenation ◽  
Optically Active ◽  
Optical Rotatory Dispersion ◽  
Rotatory Dispersion ◽  
Optical Rotatory ◽  
Combined Use ◽  
Physical And Chemical ◽  
Circular Dichroïsm ◽  
Chemical Evidence

Catalytic hydrogenation of optically active 2-pyridyl ethylcarbinol (1) formed the alkaloid conhydrine (2) stereospecifically. Application of the von Braun reaction gave conversion of (+)-conhydrine into R-(−)-3-octyl benzoate and of (−)-conhydrine into the S-(+)-antimer. Both the relative and absolute configuration of the two asymmetric centers in natural (+)-conhydrine have been determined by the combined use of optical rotatory dispersion (o.r.d.) and circular dichroism (c.d.). The results are in agreement with other physical and chemical evidence.

Optically Active Trialkynyl(phenyl)methane: Synthesis and Determination of Its Absolute Configuration by Vibrational Circular Dichroism (VCD) and Optical Rotatory Dispersion (ORD)

2010 ◽  
Vol 2010 (13) ◽  
pp. 2452-2456 ◽  
Author(s):  
Boris Buschhaus ◽  
Vito Convertino ◽  
Pablo Rivera-Fuentes ◽  
José Lorenzo Alonso-Gómez ◽  
Ana G. Petrovic ◽  
...  
Keyword(s):  
Circular Dichroism ◽  
Absolute Configuration ◽  
Optically Active ◽  
Vibrational Circular Dichroism ◽  
Optical Rotatory Dispersion ◽  
Rotatory Dispersion ◽  
Optical Rotatory ◽  
Circular Dichroïsm

Optical rotatory dispersion and circular dichroism spectra of optically active 1,1′-binaphthyl

1971 ◽  
Vol 0 (0) ◽  
pp. 3990-3992 ◽  
Author(s):  
Patricia A. Browne ◽  
Margaret M. Harris ◽  
R. Z. Mazengo ◽  
Shyam Singh
Keyword(s):  
Circular Dichroism ◽  
Optically Active ◽  
Optical Rotatory Dispersion ◽  
Rotatory Dispersion ◽  
Optical Rotatory ◽  
Circular Dichroism Spectra ◽  
Circular Dichroïsm

Synthesis, resolution, and absolute configuration of 1-phenyl-1-methyl-1-silacyclohexanone-2

1970 ◽  
Vol 48 (5) ◽  
pp. 818-823 ◽  
Author(s):  
A. G. Brook ◽  
H. W. Kucera ◽  
D. M. MacRae
Keyword(s):  
Absolute Configuration ◽  
Active Form ◽  
Dispersion Curves ◽  
Convincing Evidence ◽  
Optically Active ◽  
Optical Rotatory Dispersion ◽  
Rotatory Dispersion ◽  
Asymmetric Center ◽  
Optical Rotatory ◽  
Subsequent Oxidation

The synthesis and resolution of 1-phenyl-1-methyl-1-silacyclohexanone-2 by oxidative hydroboration of the related silacyclohexene to the silacyclohexanol, resolution of this via the strychnine salt of the phthalate half-ester, and subsequent oxidation of the silacyclohexanol to the silacyclohexanone is described. The carbon analog 1-phenyl-1-methylcyclohexanone-2 was also synthesized in optically active form. The (+)-enantiomers of the two ketones had similar optical rotatory dispersion curves, presenting convincing evidence for the identity of their configurations, and the carbon compound could be degraded without affecting the asymmetric center to (−)-(R)-2-phenyl-2-methylhexandioic acid, thereby establishing the absolute configurations of both compounds.

Optical rotatory dispersion and circular dichroism of diastereoisomers. I. The ephedrines and chloramphenicols

1969 ◽  
Vol 47 (11) ◽  
pp. 1957-1963 ◽  
Author(s):  
L. A. Mitscher ◽  
F. Kautz ◽  
J. LaPidus
Keyword(s):  
Circular Dichroism ◽  
Absorption Band ◽  
Absolute Configuration ◽  
Cotton Effect ◽  
Optical Rotatory Dispersion ◽  
Rotatory Dispersion ◽  
Optical Rotatory ◽  
Apparent Correlation ◽  
Circular Dichroïsm ◽  
Erroneous Assignment

Optical rotatory dispersion (o.r.d.) and circular dichroism measurements are reported for all four diastereoisomers in both the ephedrine and chloramphenicol series. The Cotton effect associated with the 1Lb absorption band is a reliable guide to absolute configuration in both series whereas the 1La band is not. Circular dichroism measurements are preferred as the 1La band dominates the o.r.d. curves to such an extent that erroneous assignment is quite possible. An attempt to relate the sign and intensity of the 1Lb Cotton effect with rotamer population failed due to lack of apparent correlation.

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