Copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins

Jindian Duan; Yiyang Mao; Anmei Xian; Binsen Rong; Gaochen Xu; Zhenjiang Li; Lili Zhao; Ning Zhu; Kai Guo

doi:10.1039/d0cc07995b

Copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins

Jindian Duan, Yiyang Mao, Anmei Xian, Binsen Rong, Gaochen Xu, Zhenjiang Li, Lili Zhao, Ning Zhu, Kai Guo

Nanjing Tech University

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

12 Scopus citations

Abstract

A copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins was developed, affording valuable 2,3-dihydrooxazole-spirooxindoles in moderate to good yields with excellent diastereoselectivity. The reaction sequence involves Cu(i) initiated N-O bond cleavage, 1,5-HAT and C-N bond formation. The protocol features mild reaction conditions and broad substrate scope. DFT calculations demonstrated that the [3+2] annulation pathway is more energetically favourable in both kinetics and thermodynamics.

Original language	English
Pages (from-to)	3379-3382
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	27
DOIs	https://doi.org/10.1039/d0cc07995b
State	Published - 7 Apr 2021

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title = "Copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins",

abstract = "A copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins was developed, affording valuable 2,3-dihydrooxazole-spirooxindoles in moderate to good yields with excellent diastereoselectivity. The reaction sequence involves Cu(i) initiated N-O bond cleavage, 1,5-HAT and C-N bond formation. The protocol features mild reaction conditions and broad substrate scope. DFT calculations demonstrated that the [3+2] annulation pathway is more energetically favourable in both kinetics and thermodynamics.",

author = "Jindian Duan and Yiyang Mao and Anmei Xian and Binsen Rong and Gaochen Xu and Zhenjiang Li and Lili Zhao and Ning Zhu and Kai Guo",

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T1 - Copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins

AU - Duan, Jindian

AU - Mao, Yiyang

AU - Xian, Anmei

AU - Rong, Binsen

AU - Xu, Gaochen

AU - Li, Zhenjiang

AU - Zhao, Lili

AU - Zhu, Ning

AU - Guo, Kai

PY - 2021/4/7

Y1 - 2021/4/7

N2 - A copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins was developed, affording valuable 2,3-dihydrooxazole-spirooxindoles in moderate to good yields with excellent diastereoselectivity. The reaction sequence involves Cu(i) initiated N-O bond cleavage, 1,5-HAT and C-N bond formation. The protocol features mild reaction conditions and broad substrate scope. DFT calculations demonstrated that the [3+2] annulation pathway is more energetically favourable in both kinetics and thermodynamics.

AB - A copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins was developed, affording valuable 2,3-dihydrooxazole-spirooxindoles in moderate to good yields with excellent diastereoselectivity. The reaction sequence involves Cu(i) initiated N-O bond cleavage, 1,5-HAT and C-N bond formation. The protocol features mild reaction conditions and broad substrate scope. DFT calculations demonstrated that the [3+2] annulation pathway is more energetically favourable in both kinetics and thermodynamics.

UR - http://www.scopus.com/inward/record.url?scp=85103516707&partnerID=8YFLogxK

U2 - 10.1039/d0cc07995b

DO - 10.1039/d0cc07995b

M3 - 文章

C2 - 33683244

AN - SCOPUS:85103516707

SN - 1359-7345

VL - 57

SP - 3379

EP - 3382

JO - Chemical Communications

JF - Chemical Communications

IS - 27

ER -

Copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins

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