Carbene-Catalyzed Atroposelective Annulation and Desymmetrization of Urazoles

Jiamiao Jin; Xuan Huang; Jun Xu; Tingting Li; Xiaolin Peng; Xun Zhu; Junmin Zhang; Zhichao Jin; Yonggui Robin Chi

doi:10.1021/acs.orglett.1c01191

Carbene-Catalyzed Atroposelective Annulation and Desymmetrization of Urazoles

Jiamiao Jin, Xuan Huang, Jun Xu, Tingting Li, Xiaolin Peng, Xun Zhu, Junmin Zhang, Zhichao Jin, Yonggui Robin Chi^*

^*Corresponding author for this work

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

64 Citations (Scopus)

Abstract

An NHC-catalyzed atroposelective reaction between ynals and urazoles is disclosed. The reaction establishes a chiral C-N axis via an atroposelective [3 + 2] annulation/desymmetrization process. Our reaction allows efficient access to axially chiral and heteroatom-rich urazole derivatives with potential applications in bioactive molecules and catalysis.

Original language	English
Pages (from-to)	3991-3996
Number of pages	6
Journal	Organic Letters
Volume	23
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.1c01191
Publication status	Published - May 21 2021
Externally published	Yes

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Publisher Copyright:
© 2021 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.1c01191

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title = "Carbene-Catalyzed Atroposelective Annulation and Desymmetrization of Urazoles",

abstract = "An NHC-catalyzed atroposelective reaction between ynals and urazoles is disclosed. The reaction establishes a chiral C-N axis via an atroposelective [3 + 2] annulation/desymmetrization process. Our reaction allows efficient access to axially chiral and heteroatom-rich urazole derivatives with potential applications in bioactive molecules and catalysis.",

author = "Jiamiao Jin and Xuan Huang and Jun Xu and Tingting Li and Xiaolin Peng and Xun Zhu and Junmin Zhang and Zhichao Jin and Chi, {Yonggui Robin}",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

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doi = "10.1021/acs.orglett.1c01191",

language = "English",

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T1 - Carbene-Catalyzed Atroposelective Annulation and Desymmetrization of Urazoles

AU - Jin, Jiamiao

AU - Huang, Xuan

AU - Xu, Jun

AU - Li, Tingting

AU - Peng, Xiaolin

AU - Zhu, Xun

AU - Zhang, Junmin

AU - Jin, Zhichao

AU - Chi, Yonggui Robin

PY - 2021/5/21

Y1 - 2021/5/21

N2 - An NHC-catalyzed atroposelective reaction between ynals and urazoles is disclosed. The reaction establishes a chiral C-N axis via an atroposelective [3 + 2] annulation/desymmetrization process. Our reaction allows efficient access to axially chiral and heteroatom-rich urazole derivatives with potential applications in bioactive molecules and catalysis.

AB - An NHC-catalyzed atroposelective reaction between ynals and urazoles is disclosed. The reaction establishes a chiral C-N axis via an atroposelective [3 + 2] annulation/desymmetrization process. Our reaction allows efficient access to axially chiral and heteroatom-rich urazole derivatives with potential applications in bioactive molecules and catalysis.

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U2 - 10.1021/acs.orglett.1c01191

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M3 - Article

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EP - 3996

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

Carbene-Catalyzed Atroposelective Annulation and Desymmetrization of Urazoles

Abstract

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ASJC Scopus Subject Areas

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