Asymmetric Synthesis of Spiro[isoxazolin-3,3′-oxindoles] via the Catalytic 1,3-Dipolar Cycloaddition Reaction of Nitrile Oxides

A highly enantioselective 1,3-dipolar cycloaddition of nitrile oxides with 3-arylidene-oxindoles was realized by a chiral N,N′-dioxide–nickel(II) complex catalyst under mild reaction conditions. A series of spiro-isoxazoline-oxindole derivatives were obtained in moderate yields (up to 65%) with good...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-08, Vol.79 (16), p.7703-7710
Main Authors: Lian, Xiangjin, Guo, Songsong, Wang, Gang, Lin, Lili, Liu, Xiaohua, Feng, Xiaoming
Format: Article
Language:English
Subjects:
Catalysis
Crystallography, X-Ray
Cycloaddition Reaction
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Nickel - chemistry
Nitriles - chemistry
Oxides - chemistry
Oxindoles
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
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Summary:A highly enantioselective 1,3-dipolar cycloaddition of nitrile oxides with 3-arylidene-oxindoles was realized by a chiral N,N′-dioxide–nickel(II) complex catalyst under mild reaction conditions. A series of spiro-isoxazoline-oxindole derivatives were obtained in moderate yields (up to 65%) with good regioselectivities (up to 99:1), excellent enantioselectivities (up to 99% ee), and exclusive diastereoselectivity as well.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo5012625