Catalyst-controlled switch of regioselectivity in the asymmetric allylic alkylation of oxazolones with MBHCs

A catalyst-controlled switch of regioselectivity in asymmetric allylic alkylation of oxazolones with MBHCs was described. The S N 2′-S N 2′ reaction catalysed by a quinine-derived base produced γ-selective secondary allylic oxazolone derivatives, whereas the addition-elimination reaction catalysed b...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2016-06, Vol.52 (5), p.7882-7885
Main Authors: Zhu, Gongming, Yang, Junxian, Bao, Guangjun, Zhang, Ming, Li, Jing, Li, Yiping, Sun, Wangsheng, Hong, Liang, Wang, Rui
Format: Article
Language:English
Subjects:
Adducts
Alkylation
Asymmetry
Catalysts
Derivatives
Switches
Ureas
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Summary:A catalyst-controlled switch of regioselectivity in asymmetric allylic alkylation of oxazolones with MBHCs was described. The S N 2′-S N 2′ reaction catalysed by a quinine-derived base produced γ-selective secondary allylic oxazolone derivatives, whereas the addition-elimination reaction catalysed by an amino acid-derived bifunctional urea catalyst provided β-selective primary adducts. A catalyst-controlled switch of regioselectivity in asymmetric allylic alkylation of oxazolones with MBHCs was described.
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc03246j