Concise Asymmetric Synthesis of Orthogonally Protected syn- and anti-1,3-Aminoalcohols

Novel chiral binfunctional reagents V and ent-V undergo asymmetric aldehyde allylation followed by Ir(I)-catalyzed enantioselective allylic amidation to give orthogonally protected syn- and anti-1,3-aminoalcohols with complete control of absolute and relative stereochemistry. The Mitsunobu reaction...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2013-02, Vol.15 (3), p.554-557
Main Authors: Lee, Jae Seung, Kim, Dongeun, Lozano, Lucia, Kong, Suk Bin, Han, Hyunsoo
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Amino Alcohols - chemical synthesis
Amino Alcohols - chemistry
Catalysis
Combinatorial Chemistry Techniques
Indicators and Reagents
Iridium - chemistry
Molecular Structure
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Novel chiral binfunctional reagents V and ent-V undergo asymmetric aldehyde allylation followed by Ir(I)-catalyzed enantioselective allylic amidation to give orthogonally protected syn- and anti-1,3-aminoalcohols with complete control of absolute and relative stereochemistry. The Mitsunobu reaction of the initial homoallylic alcohol products followed by Ir(I)-catalyzed enantioselective allylic amidation provides orthogonally protected syn- and anti-1,3-diamine derivatives in high yields and with excellent stereoselectivities.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol303371u