Tetrahedron letters2022，Vol.885.DOI:10.1016/j.tetlet.2021.153565

Novel preparation of chiral 3,2'-pyrrolidinyl spirooxindole from an enantioselective Michael addition between 3-(diphenylmethylene)-amino-oxindole and acrolein catalyzed by a cinchona alkaloid

Huang, Zhi-Cheng Xiang, Min Li, Wen-Sheng Zou, Ying Li, Chen-Yi Zhang, Jian Li, Xia Tian, Fang Wang, Li-Xin
Tetrahedron letters2022，Vol.885.DOI:10.1016/j.tetlet.2021.153565
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  • NSTL
  • Elsevier

Novel preparation of chiral 3,2'-pyrrolidinyl spirooxindole from an enantioselective Michael addition between 3-(diphenylmethylene)-amino-oxindole and acrolein catalyzed by a cinchona alkaloid

Huang, Zhi-Cheng 1Xiang, Min 1Li, Wen-Sheng 1Zou, Ying 1Li, Chen-Yi 1Zhang, Jian 1Li, Xia 1Tian, Fang 1Wang, Li-Xin1
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作者信息

  • 1. Chinese Acad Sci
  • 折叠

Abstract

A new type of spiro[pyrrolinyl-3,2'-oxindole] scaffolds were effectively prepared from an enantioselective Michael/cyclization between a crucial synthon of 3-(diphenylmethylene)-amino oxindole and acrolein catalyzed by a cinchona alkaloid in up to 99% total yield with up to 99% ee. Those spirooxindole aldehyde imines were reduced to new kinds of prolineamide like spirooxindole chiral amine organocatalysts. The reaction has been successfully scaled up to a gram scale and most typical organocatalysts were further purified up to 99% ee by recrystallization in their hydrochloride salts. (c) 2021 Published by Elsevier Ltd.

Key words

Asymmetric synthesis/Michael addition/cyclization/Spiro[oxindole-3/2'-pyrrolidinyl]/ASYMMETRIC-SYNTHESIS/DERIVATIVES/EFFICIENT

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出版年

2022
Tetrahedron letters

Tetrahedron letters

CCR
ISSN：0040-4039
被引量4
参考文献量33
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