Enantioselective Synthesis of Spiropyrazolone-Fused Cyclopenta[c]chromen-4-ones Bearing Five Contiguous Stereocenters via (3+2) Cycloaddition

被引：11

作者：

Khairnar, Pankaj, V ^{[1
]}

Su, Yin-Hsiang ^{[1
]}

Edukondalu, Athukuri ^{[1
]}

Lin, Wenwei ^{[1
]}

机构：

[1] Natl Taiwan Normal Univ, Dept Chem, Taipei 11677, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 17期

关键词：

ASYMMETRIC-SYNTHESIS; MICHAEL ADDITION; CASCADE; CONSTRUCTION; DERIVATIVES; PYRAZOLONES; INHIBITORS; (+/-)-HERBERTENOLIDE; ANNULATION; GENERATION;

D O I：

10.1021/acs.joc.1c01215

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective synthesis of spiropyrazolone-fused cyclopenta[c]chromen-4-ones is demonstrated via a (3+2) cycloaddition reaction. The reactions of 3-homoacylcoumarins and alpha,beta-unsaturated pyrazolones in the presence of the cinchona-alkaloid derived hydrogen-bonding catalyst provide aforementioned spiropyrazolone-chromenone adducts bearing five contiguous stereocenters, of which one is the spiro all-carbon quaternary stereocenter in high yields (up to 98%) with good to excellent stereoselectivities (>25:1 dr and up to 99% ee). This one-pot methodology could also be practically demonstrated on a gram-scale with similar efficacy.

引用

页码：12326 / 12335

页数：10

共 22 条

[21] Highly stereoselective [3+2]-cycloaddition reaction of stabilised N,N′-cyclic azomethine imines with 3-nitro-2-phenyl-2H-chromenes: Synthesis of tetrahydrochromeno[4,3-c]pyrazolo[1,2-a]pyrazol-11-ones
Barkov, Alexey Y.
Zimnitskiy, Nikolay S.
Kutyashev, Igor B.
Korotaev, Vladislav Y.
Sosnovskikh, Vyacheslav Y.
TETRAHEDRON LETTERS, 2017, 58 (42) : 3989 - 3992
[22] Synthesis of 2′,3′,4′-triaryl-5,6-dihydro-8H-spiro[indolizine-7,5′-isoxazolidin]-8-ones via 1,3-dipolar cycloaddition reaction involving (Z)-C-aryl-N-phenylnitrones
Li, Youfeng
Tang, Jin
Li, Xiaofang
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (08) : 1062 - 1066

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