Conformational control in stereoselective chemical reactions: From amino acids to iminosugars

Ari M.P. Koskinen*

*Corresponding author for this work

Research output: Contribution to journalReview Articlepeer-review

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Abstract

Two alternative synthetic strategies for the synthesis of vicinal amino alcohols from naturally occurring amino acids have been investigated, viz. one going through diastereoselective addition of organometallic species to an amino aldehyde and one going through α'-chiral α,β-enones and their diastereoselective reduction. Based on these investigations we were able to develop a synthetic strategy towards all diastereomers of deoxynojirimycin starting from naturally occurring serine through a divergent route with a late stage intermediate that can be prepared in large quantities and in enantiomerically pure form.

Original languageEnglish
Pages (from-to)609-623
Number of pages15
JournalHeterocycles
Volume103
Issue number2
Early online date22 Jan 2021
DOIs
Publication statusPublished - 2021
MoE publication typeA2 Review article, Literature review, Systematic review

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