Concise and Practical Synthesis ofC-Glycosyl Ketones from Sugar Benzothiazoles and Their Transformation into Chiral Tertiary Alcohols

2005 ◽  
Vol 70 (23) ◽  
pp. 9257-9268 ◽  
Author(s):  
Alessandro Dondoni ◽  
Nicola Catozzi ◽  
Alberto Marra
Keyword(s):  
Tertiary Alcohols ◽  
Practical Synthesis ◽  
Chiral Tertiary Alcohols

Asymmetric Synthesis of Chiral Tertiary Alcohols in High Enantiomeric Excess

1982 ◽  
pp. 37-53 ◽  
Author(s):  
ERNEST L. ELIEL ◽  
JORMA K. KOSKIMIES ◽  
BRUNO LOHRI ◽  
W. JACK FRAZEE ◽  
SUSAN MORRIS-NATSCHKE ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Enantiomeric Excess ◽  
Tertiary Alcohols ◽  
Chiral Tertiary Alcohols

Polymer-Support Synthesis of Chiral Tertiary Alcohols

Synfacts ◽  
2006 ◽  
Vol 2006 (11) ◽  
pp. 1181-1181
Author(s):  
D. Ramón ◽  
M. Yus ◽  
V. Forrat
Keyword(s):  
Polymer Support ◽  
Tertiary Alcohols ◽  
Chiral Tertiary Alcohols

scholarly journals Asymmetric Synthesis of Tertiary α -Hydroxyketones by Enantioselective Decarboxylative Chlorination and Subsequent Nucleophilic Substitution

Molecules ◽  
2020 ◽  
Vol 25 (17) ◽  
pp. 3902
Author(s):  
Mei Kee Kam ◽  
Akira Sugiyama ◽  
Ryouta Kawanishi ◽  
Kazutaka Shibatomi
Keyword(s):  
Asymmetric Synthesis ◽  
Nucleophilic Substitution ◽  
Primary Amine ◽  
Tetrabutylammonium Hydroxide ◽  
Tertiary Alcohols ◽  
Tertiary Carbon ◽  
Chiral Tertiary Alcohols

Chiral tertiary α-hydroxyketones were synthesized with high enantiopurity by asymmetric decarboxylative chlorination and subsequent nucleophilic substitution. We recently reported the asymmetric decarboxylative chlorination of β-ketocarboxylic acids in the presence of a chiral primary amine catalyst to obtain α-chloroketones with high enantiopurity. Here, we found that nucleophilic substitution of the resulting α-chloroketones with tetrabutylammonium hydroxide yielded the corresponding α-hydroxyketones without loss of enantiopurity. The reaction proceeded smoothly even at a tertiary carbon. The proposed method would be useful for the preparation of chiral tertiary alcohols.

scholarly journals A practical synthesis of long-chain iso-fatty acids (iso-C12–C19) and related natural products

2013 ◽  
Vol 9 ◽  
pp. 1807-1812 ◽  
Author(s):  
Mark B Richardson ◽  
Spencer J Williams
Keyword(s):  
Fatty Acids ◽  
Natural Products ◽  
Selective Reduction ◽  
Isopropyl Group ◽  
Tertiary Alcohols ◽  
Practical Synthesis ◽  
Long Chain

A gram-scale synthesis of terminally-branched iso-fatty acids (iso-C12–C19) was developed commencing with methyl undec-10-enoate (methyl undecylenate) (for iso-C12–C14) or the C15and C16lactones pentadecanolide (for iso-C15–C17) and hexadecanolide (for iso-C18–C19). Central to the approaches outlined is the two-step construction of the terminal isopropyl group through addition of methylmagnesium bromide to the ester/lactones and selective reduction of the resulting tertiary alcohols. Thus, the C12, C17and C18iso-fatty acids were obtained in three steps from commercially-available starting materials, and the remaining C13–C16and C19iso-fatty acids were prepared by homologation or recursive dehomologations of these fatty acids or through intercepting appropriate intermediates. Highlighting the synthetic potential of the iso-fatty acids and various intermediates prepared herein, we describe the synthesis of the natural products (S)-2,15-dimethylpalmitic acid, (S)-2-hydroxy-15-methylpalmitic acid, and 2-oxo-14-methylpentadecane.

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