Preparation and Utilization of Contiguous Bisaziridines as Chiral Building Blocks

Chiral contiguous bisaziridines were prepared by the aziridination of chiral 3‐[1‐(1‐phenylethyl)aziridin‐2‐yl)]acrylaldehydes with either N‐Boc‐O‐tosyl or N‐Ts‐O‐tosyl hydroxylamine as a nitrogen source and (2R)‐ or (2S)‐[diphenyl(trimethylsilyloxy)methyl]pyrrolidine as a chiral organocatalyst. The...

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Bibliographic Details
Published in:	Advanced synthesis & catalysis Vol. 363; no. 13; pp. 3250 - 3257
Main Authors:	Rhee, Hyong‐Jin, Ranjith, Jala, Byeon, Huimyoung, Ha, Hyun‐Joon, Yang, Jung Woon
Format:	Journal Article
Language:	English
Published:	Heidelberg Wiley Subscription Services, Inc 01-07-2021
Subjects:	Aziridination Chiral building block Contiguous bisaziridine Nitrogen Organocatalysis Ring opening Ring-opening reaction
Online Access:	Get full text
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Summary:	Chiral contiguous bisaziridines were prepared by the aziridination of chiral 3‐[1‐(1‐phenylethyl)aziridin‐2‐yl)]acrylaldehydes with either N‐Boc‐O‐tosyl or N‐Ts‐O‐tosyl hydroxylamine as a nitrogen source and (2R)‐ or (2S)‐[diphenyl(trimethylsilyloxy)methyl]pyrrolidine as a chiral organocatalyst. The regioselective ring opening of bisaziridines afforded chiral nitrogen‐rich molecules.
Bibliography:	These authors contributed equally to this work.
ISSN:	1615-4150 1615-4169
DOI:	10.1002/adsc.202100335