ChemInform Abstract: Asymmetric Synthesis of Tertiary Alcohols from α-Halo Boronic Esters.

ChemInform ◽  
1990 ◽  
Vol 21 (10) ◽  
Author(s):  
D. S. MATTESON ◽  
G. D. HURST
Keyword(s):  
Asymmetric Synthesis ◽  
Tertiary Alcohols ◽  
Boronic Esters

Asymmetric synthesis of tertiary alcohols from ?-halo boronic esters

1990 ◽  
Vol 1 (1) ◽  
pp. 65-74 ◽  
Author(s):  
Donald S. Matteson ◽  
Gerald D. Hurst
Keyword(s):  
Asymmetric Synthesis ◽  
Tertiary Alcohols ◽  
Boronic Esters

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

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.

α-Halo boronic esters in asymmetric synthesis

Tetrahedron ◽  
1998 ◽  
Vol 54 (36) ◽  
pp. 10555-10607 ◽  
Author(s):  
Donald S. Matteson
Keyword(s):  
Asymmetric Synthesis ◽  
Boronic Esters

scholarly journals Asymmetric Synthesis of Secondary and Tertiary Boronic Esters

2017 ◽  
Vol 56 (39) ◽  
pp. 11700-11733 ◽  
Author(s):  
Beatrice S. L. Collins ◽  
Claire M. Wilson ◽  
Eddie L. Myers ◽  
Varinder K. Aggarwal
Keyword(s):  
Asymmetric Synthesis ◽  
Boronic Esters
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