Direct Asymmetric Vinylogous Mannich Addition of 3,5-Disubstituted-4-nitroisoxazoles to Isatin-Derived Imines Catalyzed by a Bifunctional Phase-Transfer-Catalyst

Asymmetric Mannich-type addition of 3,5-disubstituted-4-nitroisoxazoles to isatin-derived Boc-protected imines has been realized by using 0.01 equiv of amide phosphonium salt as a phase transfer catalyst. Our current methodology allows for the formation of 3-isoxazolylmethyl-substituted 3-aminooxind...

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Published inJournal of organic chemistry Vol. 83; no. 23; pp. 14617 - 14625
Main Authors Xia, Xuejian, Zhu, Qiongqiong, Wang, Jing, Chen, Jie, Cao, Weiguo, Zhu, Bo, Wu, Xiaoyu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.12.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ANTAGONIST
ENANTIOSELECTIVE SYNTHESIS
4-NITROISOXAZOLES
PROLIFERATION
KETIMINES
DERIVATIVES
HIGHLY EFFICIENT
DISCOVERY
CONJUGATE ADDITION
MICHAEL ADDITION
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Summary:Asymmetric Mannich-type addition of 3,5-disubstituted-4-nitroisoxazoles to isatin-derived Boc-protected imines has been realized by using 0.01 equiv of amide phosphonium salt as a phase transfer catalyst. Our current methodology allows for the formation of 3-isoxazolylmethyl-substituted 3-aminooxindoles in excellent yields with good to excellent enantioselectivities. The practical value of this methodology was exemplified by a gram-scale synthesis of 5an, a key intermediate for the formal synthesis (+)-AG-041R.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.8b02439