Enantioreversal in the Sharpless Asymmetric Epoxidation Reaction Controlled by the Molecular Weight of a Covalently Appended Achiral Polymer

2005 ◽  
Vol 70 (5) ◽  
pp. 1728-1731 ◽  
Author(s):  
Neal N. Reed ◽  
Tobin J. Dickerson ◽  
Grant E. Boldt ◽  
Kim D. Janda
Keyword(s):  
Molecular Weight ◽  
Asymmetric Epoxidation ◽  
Epoxidation Reaction ◽  
Sharpless Asymmetric Epoxidation

Facile synthesis of the enantiomers of frontalin

1984 ◽  
Vol 62 (11) ◽  
pp. 2148-2154 ◽  
Author(s):  
B. D. Johnston ◽  
A. C. Oehlschlager
Keyword(s):  
Asymmetric Epoxidation ◽  
Facile Synthesis ◽  
Epoxidation Reaction ◽  
Synthetic Sequence ◽  
Sharpless Asymmetric Epoxidation

S-(−)- and R-(+)-frontalin (1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane) were prepared from (E)-2-methyl-2,6-heptadiene-1-ol utilizing the Sharpless asymmetric epoxidation reaction to induce chirality. The six-step synthetic sequence proceeded in approximately 50% overall yield and was found to be suitable for the preparation of multi-gram quantities of either enantiomer with ≥ 90% ee.

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