Asymmetric Azo-ene Reactions Using the Chiral Azo-enophile Di-(-)-(1R,2S)-2-phenyl-1-cyclohexyl Diazenedicarboxylate

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Title

Asymmetric Azo-ene Reactions Using the Chiral Azo-enophile Di-(-)-(1R,2S)-2-phenyl-1-cyclohexyl Diazenedicarboxylate

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The University of Auckland Library

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Description

The preparation of di-(−)-(1R,2S)-2-phenyl-1-cyclohexyl diazenedicarboxylate 4 is described. Reaction of (1R,2S)-2-phenyl-1-cyclohexanol 1 with excess phosgene in the presence of quinoline afforded chloroformate 2 which was treated directly with hydrazine monohydrate (0.5 equiv.) to afford di-(−)-(1R,2S)-2-phenyl-1-cyclohexyl diazanedicarboxylate 3. Oxidization of 3 to the azo-enophile 4 was then readily effected in high yield using N-bromosuccinimide and pyridine. The azo-ene reactions of 4 ...

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Format

Research paper

Research format

Journal article

Date created

1998

Creator

Brimble, Margaret / Lee, CY

URL

http://hdl.handle.net/2292/8075

Related subjects

ELECTROPHILIC AMINATION REACTIONS / ALLYLIC AMINATION / ORGANIC-SYNTHESIS / ACHIRAL ESTER / AZODICARBOXYLATE / DIAZANEDICARBOXYLATE / INDUCTION / OXIDATION / ALKENES

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