In:
Angewandte Chemie, Wiley, Vol. 131, No. 9 ( 2019-02-25), p. 2865-2869
Abstract:
A DMAP‐ N ‐oxide, featuring an α‐amino acid as the chiral source, was developed, synthesized and applied in asymmetric Steglich rearrangement. A series of O‐acylated azlactones afforded C‐acylated azlactones possessing a quaternary stereocenter in high yields (up to 97 % yield) and excellent enantioselectivities (up to 97 % ee ). Compared to the widespread use of pyridine nitrogen, which serves as the nucleophilic site in the asymmetric acyl transfer reaction, we discovered that chiral DMAP‐ N ‐oxides, in which the oxygen now acts as the nucleophilic site, are efficient acyl transfer catalysts. Our finding might open a new door for the development of chiral DMAP‐ N ‐oxides for asymmetric acyl transfer reactions.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.201812864
Language:
English
Publisher:
Wiley
Publication Date:
2019
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514305-6
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505872-7
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1479266-7
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506259-7
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