Quinoline alkaloids. Part XIV. Asymmetric synthesis by the peroxy-acid–olefin reaction. The absolute stereochemistry of balfourodine, isobalfourodine, and related compounds, and the biosynthesis of isomeric dihydrofuro- and dihydropyrano-derivatives

1973 ◽  
pp. 626-632 ◽  
Author(s):  
Robert M. Bowman ◽  
James F. Collins ◽  
Michael F. Grundon
Keyword(s):  
Asymmetric Synthesis ◽  
Peroxy Acid ◽  
Quinoline Alkaloids ◽  
The Absolute ◽  
Related Compounds ◽  
Absolute Stereochemistry

The absolute configuration of (+)-3,4-Bis(p-hydroxyphenyl)hexane (hexoestrol) and related compounds

1974 ◽  
Vol 27 (8) ◽  
pp. 1753 ◽  
Author(s):  
DJ Collins ◽  
JJ Hobbs
Keyword(s):  
Absolute Configuration ◽  
Valeric Acid ◽  
The Absolute ◽  
Related Compounds ◽  
Absolute Stereochemistry

(+)-(2S,3R)-2,3-Bis(p-methoxyphenyl)valeric acid, previously converted into (-)-(2R,3R)-2,3-bis(p-methoxyphenyl)pentane, has now been converted into (+)-(3R,4R)-3,4-bis(p-methoxyphenyl)hexane via (+)-(3S,4R)-3,4-bis(p-methoxyphenyl)hexan-2-one and (-)-(4s)-3,4-bis(p-methoxypheny1)hex-2-ene. This provides unequivocal correlation of the absolute stereochemistry of a series of homologous diarylalkanes, and a corresponding series of diarylalkenes.

Asymmetric synthesis via chiral transition metal auxiliaries

1988 ◽  
Vol 326 (1592) ◽  
pp. 619-631 ◽  
Keyword(s):  
Asymmetric Synthesis ◽  
Bond Formation ◽  
Complete Control ◽  
Chromium Tricarbonyl ◽  
Chiral Transition ◽  
Carbon Carbon Bond ◽  
The Absolute ◽  
Arene Chromium Tricarbonyl ◽  
Amphetamine Derivatives ◽  
Absolute Stereochemistry

Stoichiometric reagents for the control of the absolute stereochemistry of new chiral centres produced during reactions involving carbon-carbon bond formation are described. Chiral iron acyl reagents act as chiral equivalents of a variety of carbonyl functionalities and their potential for asymmetric synthesis can be illustrated for pseudopeptides, amino acids, P-lactams, y-lactams and lactones. A simple methodology based on arene chromium tricarbonyl chemistry allows the elaboration of benzylic chiral centres with complete control over the absolute stereochemistry. This may be illustrated, for example, by the conversion of amphetamine derivatives into pseudoephedrines.

scholarly journals Asymmetric Synthesis of 1,2-Limonene Epoxides by Jacobsen Epoxidation

2021 ◽  
Vol 03 (03) ◽  
pp. e113-e118
Author(s):  
Zi-Yi Huang ◽  
Min-Ru Jiao ◽  
Xiu Gu ◽  
Zi-Ran Zhai ◽  
Jian-Qi Li ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Raw Materials ◽  
The Absolute ◽  
Diastereomeric Excess ◽  
Absolute Stereochemistry

This study reported an asymmetric synthesis of 1,2-limonene epoxides. The absolute stereochemistry was controlled by a Jacobsen epoxidation of cis-1,2-limonene epoxide (with diastereomeric excess of 98%) and trans-1,2-limonene epoxide (with diastereomeric excess of 94%), which could be used as important raw materials for the preparation of related cannabinoid drugs.

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