Stereoselective oxindole synthesis by palladium-catalyzed cyclization reaction of 2-(alkynyl)aryl isocyanates with amides

Tomoya Miura; Takeharu Toyoshima; Yusuke Takahashi; Masahiro Murakami

doi:10.1021/ol900759f

Stereoselective oxindole synthesis by palladium-catalyzed cyclization reaction of 2-(alkynyl)aryl isocyanates with amides

Tomoya Miura, Takeharu Toyoshima, Yusuke Takahashi, Masahiro Murakami

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

39 Citations (Scopus)

Abstract

A new cyclization reaction occurred on treatment of 2-(alkynyl)aryl isocyanates with amides in the presence of a palladium(0)/diphosphine catalyst to stereoselectively form 3-(amidoalkylidene)oxindoles. A carbon-nitrogen bond as well as a carbon-carbon bond were simultaneously introduced onto the alkyne moiety to construct an oxindole skeleton with stereoselective placement of the amino substituent cis to the carbonyl group.

Original language	English
Pages (from-to)	2141-2143
Number of pages	3
Journal	Organic Letters
Volume	11
Issue number	10
DOIs	https://doi.org/10.1021/ol900759f
Publication status	Published - May 21 2009
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol900759f

Cite this

@article{6499106c662345a4993fc64c68b354b0,

title = "Stereoselective oxindole synthesis by palladium-catalyzed cyclization reaction of 2-(alkynyl)aryl isocyanates with amides",

abstract = "A new cyclization reaction occurred on treatment of 2-(alkynyl)aryl isocyanates with amides in the presence of a palladium(0)/diphosphine catalyst to stereoselectively form 3-(amidoalkylidene)oxindoles. A carbon-nitrogen bond as well as a carbon-carbon bond were simultaneously introduced onto the alkyne moiety to construct an oxindole skeleton with stereoselective placement of the amino substituent cis to the carbonyl group.",

author = "Tomoya Miura and Takeharu Toyoshima and Yusuke Takahashi and Masahiro Murakami",

year = "2009",

month = may,

day = "21",

doi = "10.1021/ol900759f",

language = "English",

volume = "11",

pages = "2141--2143",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "10",

}

TY - JOUR

T1 - Stereoselective oxindole synthesis by palladium-catalyzed cyclization reaction of 2-(alkynyl)aryl isocyanates with amides

AU - Miura, Tomoya

AU - Toyoshima, Takeharu

AU - Takahashi, Yusuke

AU - Murakami, Masahiro

PY - 2009/5/21

Y1 - 2009/5/21

N2 - A new cyclization reaction occurred on treatment of 2-(alkynyl)aryl isocyanates with amides in the presence of a palladium(0)/diphosphine catalyst to stereoselectively form 3-(amidoalkylidene)oxindoles. A carbon-nitrogen bond as well as a carbon-carbon bond were simultaneously introduced onto the alkyne moiety to construct an oxindole skeleton with stereoselective placement of the amino substituent cis to the carbonyl group.

AB - A new cyclization reaction occurred on treatment of 2-(alkynyl)aryl isocyanates with amides in the presence of a palladium(0)/diphosphine catalyst to stereoselectively form 3-(amidoalkylidene)oxindoles. A carbon-nitrogen bond as well as a carbon-carbon bond were simultaneously introduced onto the alkyne moiety to construct an oxindole skeleton with stereoselective placement of the amino substituent cis to the carbonyl group.

UR - http://www.scopus.com/inward/record.url?scp=66149092660&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=66149092660&partnerID=8YFLogxK

U2 - 10.1021/ol900759f

DO - 10.1021/ol900759f

M3 - Article

AN - SCOPUS:66149092660

SN - 1523-7060

VL - 11

SP - 2141

EP - 2143

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

Stereoselective oxindole synthesis by palladium-catalyzed cyclization reaction of 2-(alkynyl)aryl isocyanates with amides

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this