Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Review | Special issue | Vol 103, No. 2, 2021, pp.609-623
Published online, 22nd January, 2021
DOI: 10.3987/REV-20-SR(K)7
Conformational Control in Stereoselective Chemical Reactions: From Amino Acids to Iminosugars

Ari Koskinen*

*Department of Chemistry and Material Sciences, Aalto University, Finland


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.