LiAlH 4 ‐Induced Selective Ring Rearrangement of 2‐(2‐Cyanoethyl)aziridines toward 2‐(Aminomethyl)pyrrolidines and 3‐Aminopiperidines as Eligible Heterocyclic Building Blocks | Zendy

Dolfen Jeroen | Zendy; Vervisch Karel | Zendy; De Kimpe Norbert | Zendy; D'hooghe Matthias | Zendy

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LiAlH 4 ‐Induced Selective Ring Rearrangement of 2‐(2‐Cyanoethyl)aziridines toward 2‐(Aminomethyl)pyrrolidines and 3‐Aminopiperidines as Eligible Heterocyclic Building Blocks

Author(s) -

Dolfen Jeroen,

Vervisch Karel,

De Kimpe Norbert,

D'hooghe Matthias

Publication year - 2016

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201504853

Subject(s) - ring (chemistry) , chemistry , stereoselectivity , stereochemistry , aryl , combinatorial chemistry , organic chemistry , catalysis , alkyl

2‐(2‐Cyanoethyl)aziridines and 2‐aryl‐3‐(2‐cyanoethyl)aziridines were deployed as substrates for an In(OTf) 3 ‐mediated regio‐ and stereoselective ring rearrangement upon treatment with LiAlH 4 , affording a variety of novel 2‐(aminomethyl)pyrrolidines and 3‐aminopiperidines, respectively. Further synthetic elaboration of the obtained 3‐aminopiperidines resulted in the formation of a peculiar and unexplored conformationally constrained imidazolidinone and diketopiperazine scaffold.

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