A hydrogen borrowing annulation strategy for the stereocontrolled synthesis of saturated aza-heterocycles

An iridium catalyzed method for the synthesis of saturated aza-heterocycles from amines and diols is reported. A wide range of substituted heterocycles can be obtained using this approach including products bearing substituents at the C2, C3 and C4 positions. Employing water as the solvent, enantiop...

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Published inChemical communications (Cambridge, England) Vol. 56; no. 24; pp. 3563 - 3566
Main Authors Chamberlain, Anna E. R., Paterson, Kieran J., Armstrong, Roly J., Twin, Heather C., Donohoe, Timothy J.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 25.03.2020
Royal Society of Chemistry
Subjects
Amines
Chemical reactions
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Diols
Iridium
Organic chemistry
Physical Sciences
Racemization
Science & Technology
Substitutes
ALCOHOLS
FUNCTIONALIZATION
CATALYZED N-HETEROCYCLIZATION
COMPLEX
ACTIVATION
AMINATION
TERTIARY-AMINES
ALKYLATION
SECONDARY
C-H
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Summary:An iridium catalyzed method for the synthesis of saturated aza-heterocycles from amines and diols is reported. A wide range of substituted heterocycles can be obtained using this approach including products bearing substituents at the C2, C3 and C4 positions. Employing water as the solvent, enantiopure diols could undergo annulation with minimal racemization, enabling the synthesis of valuable enantioenriched C3 and C4-substituted saturated aza-heterocycles.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc00903b