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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 11, Number 4
BKCSDE 11(4)
April 20, 1990 

 
Title
Stereoselective Reduction of Methyl Vinyl Ketone Dimer
Author
Jong-Gab Jun*, Dong Gyun Shin, Chang Kiu Lee, Kwan Seog Sin
Keywords
Abstract
The stereoselectivity of the reaction between methyl vinyl ketone dimer, which contains two possible sites of chelation, and zinc borohydride or diisobutylaluminum hydride has been studied in order to illuminate the factors involved in the high levels of asymmetric induction obtained in the bicyclic system. The conditions for the formation of the exo-5,7-dimethyl-6,8-dioxabicyclo[3.2.1]octane are DIBAH reduction of MVK dimer in ether at reflux followed by acidic cyclizatioan, and for the endo isomer are Zn(BH4)2 reduction with ZnCl2 at 0℃.
Page
307 - 309
Full Text
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