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Highly efficient asymmetric trans-selective aziridination of diazoacetamides and N-Boc-imines catalyzed by chiral Brønsted acids.
MedLine Citation:
PMID:  19534488     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
A clean and fast (10 min) aziridination of diazoacetamides with N-Boc-imines, as well as N-Cbz-imines, catalyzed by chiral phosphoric acid (R)-5g in DCM at room temperature was developed. The excellent yields (89-97%), diastereoselectivities (trans/cis > 50:1), chemoselectivities (3:4 = >95:5), and enantioselectivities (88-98% ee) were achieved in the reaction.
Authors:
Xiaofei Zeng; Xin Zeng; Zhenjiang Xu; Min Lu; Guofu Zhong
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Organic letters     Volume:  11     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2009 Jul 
Date Detail:
Created Date:  2009-07-09     Completed Date:  2009-08-13     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  3036-9     Citation Subset:  -    
Affiliation:
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang link, Singapore 637371, Singapore.
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