Divergent Metal-Free [4 + 2] Cascade Reaction of 1-Indanylidenemalononitrile with 3-Benzylidenebenzofuran-2(3 H)-one: Access to Spiro-dihydrofluorene-benzofuranone and Axially Chiral Fluorenylamine-phenol Derivatives

Ran Li; Lei Yao; Yan Bo Wang; Jun Yan Zhu; Lixiong Zhang; Ji Ya Fu; Chuan Bao Zhang; Lili Zhao

doi:10.1021/acs.orglett.1c01510

Divergent Metal-Free [4 + 2] Cascade Reaction of 1-Indanylidenemalononitrile with 3-Benzylidenebenzofuran-2(3 H)-one: Access to Spiro-dihydrofluorene-benzofuranone and Axially Chiral Fluorenylamine-phenol Derivatives

Ran Li, Lei Yao, Yan Bo Wang, Jun Yan Zhu, Lixiong Zhang, Ji Ya Fu, Chuan Bao Zhang, Lili Zhao

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

An efficient cascade reaction of 1-indanylidenemalononitrile with 3-benzylidenebenzofuran-2(3H)-one divergently promoted by DABCO or chiral organocatalyst was developed under mild reaction conditions, and various spiro-dihydrofluorene-benzofuranones were produced in gratifying results, respectively. It is worth noting that both the spiro and axially chiral products can be obtained by tuning the reaction conditions. The mechanism of the transformation was also studied by quantum chemical calculations.

Original language	English
Pages (from-to)	5611-5615
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.1c01510
State	Published - 6 Aug 2021

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Li, R., Yao, L., Wang, Y. B., Zhu, J. Y., Zhang, L., Fu, J. Y., Zhang, C. B., & Zhao, L. (2021). Divergent Metal-Free [4 + 2] Cascade Reaction of 1-Indanylidenemalononitrile with 3-Benzylidenebenzofuran-2(3 H)-one: Access to Spiro-dihydrofluorene-benzofuranone and Axially Chiral Fluorenylamine-phenol Derivatives. Organic Letters, 23(15), 5611-5615. https://doi.org/10.1021/acs.orglett.1c01510

@article{bfd6c2dd793942a6ad2610ca0ba0766f,

title = "Divergent Metal-Free [4 + 2] Cascade Reaction of 1-Indanylidenemalononitrile with 3-Benzylidenebenzofuran-2(3 H)-one: Access to Spiro-dihydrofluorene-benzofuranone and Axially Chiral Fluorenylamine-phenol Derivatives",

abstract = "An efficient cascade reaction of 1-indanylidenemalononitrile with 3-benzylidenebenzofuran-2(3H)-one divergently promoted by DABCO or chiral organocatalyst was developed under mild reaction conditions, and various spiro-dihydrofluorene-benzofuranones were produced in gratifying results, respectively. It is worth noting that both the spiro and axially chiral products can be obtained by tuning the reaction conditions. The mechanism of the transformation was also studied by quantum chemical calculations.",

author = "Ran Li and Lei Yao and Wang, {Yan Bo} and Zhu, {Jun Yan} and Lixiong Zhang and Fu, {Ji Ya} and Zhang, {Chuan Bao} and Lili Zhao",

note = "Publisher Copyright: {\textcopyright} ",

year = "2021",

month = aug,

day = "6",

doi = "10.1021/acs.orglett.1c01510",

language = "英语",

volume = "23",

pages = "5611--5615",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "15",

}

Li, R, Yao, L, Wang, YB, Zhu, JY, Zhang, L, Fu, JY, Zhang, CB & Zhao, L 2021, 'Divergent Metal-Free [4 + 2] Cascade Reaction of 1-Indanylidenemalononitrile with 3-Benzylidenebenzofuran-2(3 H)-one: Access to Spiro-dihydrofluorene-benzofuranone and Axially Chiral Fluorenylamine-phenol Derivatives', Organic Letters, vol. 23, no. 15, pp. 5611-5615. https://doi.org/10.1021/acs.orglett.1c01510

Divergent Metal-Free [4 + 2] Cascade Reaction of 1-Indanylidenemalononitrile with 3-Benzylidenebenzofuran-2(3 H)-one: Access to Spiro-dihydrofluorene-benzofuranone and Axially Chiral Fluorenylamine-phenol Derivatives. / Li, Ran; Yao, Lei; Wang, Yan Bo et al.
In: Organic Letters, Vol. 23, No. 15, 06.08.2021, p. 5611-5615.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Divergent Metal-Free [4 + 2] Cascade Reaction of 1-Indanylidenemalononitrile with 3-Benzylidenebenzofuran-2(3 H)-one

T2 - Access to Spiro-dihydrofluorene-benzofuranone and Axially Chiral Fluorenylamine-phenol Derivatives

AU - Li, Ran

AU - Yao, Lei

AU - Wang, Yan Bo

AU - Zhu, Jun Yan

AU - Zhang, Lixiong

AU - Fu, Ji Ya

AU - Zhang, Chuan Bao

AU - Zhao, Lili

PY - 2021/8/6

Y1 - 2021/8/6

N2 - An efficient cascade reaction of 1-indanylidenemalononitrile with 3-benzylidenebenzofuran-2(3H)-one divergently promoted by DABCO or chiral organocatalyst was developed under mild reaction conditions, and various spiro-dihydrofluorene-benzofuranones were produced in gratifying results, respectively. It is worth noting that both the spiro and axially chiral products can be obtained by tuning the reaction conditions. The mechanism of the transformation was also studied by quantum chemical calculations.

AB - An efficient cascade reaction of 1-indanylidenemalononitrile with 3-benzylidenebenzofuran-2(3H)-one divergently promoted by DABCO or chiral organocatalyst was developed under mild reaction conditions, and various spiro-dihydrofluorene-benzofuranones were produced in gratifying results, respectively. It is worth noting that both the spiro and axially chiral products can be obtained by tuning the reaction conditions. The mechanism of the transformation was also studied by quantum chemical calculations.

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DO - 10.1021/acs.orglett.1c01510

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SN - 1523-7060

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SP - 5611

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JO - Organic Letters

JF - Organic Letters

IS - 15

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Divergent Metal-Free [4 + 2] Cascade Reaction of 1-Indanylidenemalononitrile with 3-Benzylidenebenzofuran-2(3 H)-one: Access to Spiro-dihydrofluorene-benzofuranone and Axially Chiral Fluorenylamine-phenol Derivatives

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