Stereospecific Construction of Chiral Quaternary Carbon Compounds from Chiral Secondary Alcohol Derivatives

Chiral tertiary dichloromethylcarbinol derivatives, prepared by stereospecific α C–H insertion reaction of dichlorocarbene with protected chiral secondary alcohols, were converted into intermediary α-chloroepoxides which gave stereospecifically chiral quaternary carbon compounds, α-aminoacids via α-...

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Bibliographic Details
Published in:Chemistry letters 2003-01, Vol.32 (1), p.4-5
Main Authors: Masaki, Yukio, Arasaki, Hideki, Iwata, Masashi
Format: Article
Language:English
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Summary:Chiral tertiary dichloromethylcarbinol derivatives, prepared by stereospecific α C–H insertion reaction of dichlorocarbene with protected chiral secondary alcohols, were converted into intermediary α-chloroepoxides which gave stereospecifically chiral quaternary carbon compounds, α-aminoacids via α-azide-aldehydes and α-cyanoacetic acids through cyanation, respectively. The fashion generating the quaternary centers from dichloromethylcarbinols via α-chloroepoxides was proved to be quite different depending on the substrates: inversion of configuration of non-benzylic substrates and apparent retention with benzylic one.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2003.4