Rhodium-Catalyzed Sequential Cycloisomerization/Aldol Addition of Cyclopropene Carboxylic Acids with Isatins

Dan Zhang; Xin Wang; Mengchu Zhang; Wenhao Hu

doi:10.1021/acs.orglett.0c01957

Rhodium-Catalyzed Sequential Cycloisomerization/Aldol Addition of Cyclopropene Carboxylic Acids with Isatins

Dan Zhang^*
, Xin Wang
, Mengchu Zhang
, Wenhao Hu^*

^*Corresponding author for this work

Sun Yat-Sen University

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

14 Scopus citations

Abstract

A unique, rhodium-catalyzed reaction of cyclopropene carboxylic acids with isatins has been developed, which takes place through a trapping process of transient cyclic carboxylic oxonium ylides. This reaction tolerates a wide variety of cyclopropene carboxylic acids and N-protected or unprotected isatins and represents a new, direct strategy to access valuable γ-substituted γ-butenolide architectures containing an oxindole moiety in very high yields under mild reaction conditions.

Original language	English
Pages (from-to)	5600-5604
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.0c01957
State	Published - 17 Jul 2020
Externally published	Yes

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title = "Rhodium-Catalyzed Sequential Cycloisomerization/Aldol Addition of Cyclopropene Carboxylic Acids with Isatins",

abstract = "A unique, rhodium-catalyzed reaction of cyclopropene carboxylic acids with isatins has been developed, which takes place through a trapping process of transient cyclic carboxylic oxonium ylides. This reaction tolerates a wide variety of cyclopropene carboxylic acids and N-protected or unprotected isatins and represents a new, direct strategy to access valuable γ-substituted γ-butenolide architectures containing an oxindole moiety in very high yields under mild reaction conditions.",

author = "Dan Zhang and Xin Wang and Mengchu Zhang and Wenhao Hu",

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

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doi = "10.1021/acs.orglett.0c01957",

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T1 - Rhodium-Catalyzed Sequential Cycloisomerization/Aldol Addition of Cyclopropene Carboxylic Acids with Isatins

AU - Zhang, Dan

AU - Wang, Xin

AU - Zhang, Mengchu

AU - Hu, Wenhao

PY - 2020/7/17

Y1 - 2020/7/17

N2 - A unique, rhodium-catalyzed reaction of cyclopropene carboxylic acids with isatins has been developed, which takes place through a trapping process of transient cyclic carboxylic oxonium ylides. This reaction tolerates a wide variety of cyclopropene carboxylic acids and N-protected or unprotected isatins and represents a new, direct strategy to access valuable γ-substituted γ-butenolide architectures containing an oxindole moiety in very high yields under mild reaction conditions.

AB - A unique, rhodium-catalyzed reaction of cyclopropene carboxylic acids with isatins has been developed, which takes place through a trapping process of transient cyclic carboxylic oxonium ylides. This reaction tolerates a wide variety of cyclopropene carboxylic acids and N-protected or unprotected isatins and represents a new, direct strategy to access valuable γ-substituted γ-butenolide architectures containing an oxindole moiety in very high yields under mild reaction conditions.

UR - https://www.scopus.com/pages/publications/85088148270

U2 - 10.1021/acs.orglett.0c01957

DO - 10.1021/acs.orglett.0c01957

M3 - 文章

C2 - 32628497

AN - SCOPUS:85088148270

SN - 1523-7060

VL - 22

SP - 5600

EP - 5604

JO - Organic Letters

JF - Organic Letters

IS - 14

ER -

Rhodium-Catalyzed Sequential Cycloisomerization/Aldol Addition of Cyclopropene Carboxylic Acids with Isatins

Abstract

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