10.1002/anie.201712785
Angewandte Chemie International Edition
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procedure,[20] 3c was successfully converted to chiral oxazoline
5, which could further yield chiral amino-alcohols (Scheme 3a).
The reaction of 3c with hydrogen chloride in THF gave β-chloro-
α-aminoketone 6 in good yield (Scheme 3b).[21] On the other
hand, the transformation of tosylated aziridine intermediate 7
prepared from 3a could further allow generating β-amino-α-
hydroxyketone 8 (Scheme 3c).[22]
Synthesis (Ed.: A. K. Yudin), Wiley-VCH, Weinheim, 2006, Chap. 11, p.
399.
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Scheme 3. Synthetic elaboration.
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In summary, we have successfully developed a new NHC-
catalyzed aza-benzoin reaction of aldehydes with 2H-azirines,
paving an avenue for synthetic chemists to build various chiral
aziridines in high yields with excellent enantioselectivities. This
new protocol allows the rapid assembly of optically active
aziridines from simple and readily available starting materials
under mild conditions. Further investigations on 2H-azirines as
starting materials in asymmetric synthesis, as well as a detailed
mechanistic study, are currently underway in our laboratory.
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Acknowledgements
Generous financial supports for this work are provided by: the
National Natural Science Foundation of China (21672121), the
“Thousand Plan” Youth program of China, the Tsinghua
University, the Bayer Investigator fellow, the fellowship of
Tsinghua-Peking centre for life sciences (CLS).
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Conflict of interest
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Urrios, Synthesis 1988, 314; b) J. A. Murry, D. E. Frantz, A. Soheili, R.
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The authors declare no conflict of interest.
Keywords: aza-benzoin
•
2H-azirine
•
aziridine
•
N-
hetereocyclic carbene • asymmetric catalysis
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[2] “Aziridine Natural Product
–
Discovery, Biological Activity and
Biosynthesis”: P. A. S. Lowden in Aziridines and Epoxides in Organic
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