Cyclization reaction of cyano-substituted unsaturated esters prompted by conjugate addition of organoborons

Tomoya Miura; Tatsuro Harumashi; Masahiro Murakami

doi:10.1021/ol062882y

Cyclization reaction of cyano-substituted unsaturated esters prompted by conjugate addition of organoborons

Tomoya Miura, Tatsuro Harumashi, Masahiro Murakami

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

37 Citations (Scopus)

Abstract

(Chemical Equation Presented) Unsaturated esters possessing a pendent cyano moiety react with B-Ar-9-BBNs in the presence of a rhodium(I) catalyst to give the five- and six-membered β-enamino esters in good yield. An (oxa-π-allyl)rhodium(I) intermediate, formed by initial conjugate addition of an Ar-rhodium(I) species, undergoes a facile intramolecular addition to the cyano group to construct the carbocyclic skeletons.

Original language	English
Pages (from-to)	741-743
Number of pages	3
Journal	Organic Letters
Volume	9
Issue number	5
DOIs	https://doi.org/10.1021/ol062882y
Publication status	Published - Mar 1 2007
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol062882y

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abstract = "(Chemical Equation Presented) Unsaturated esters possessing a pendent cyano moiety react with B-Ar-9-BBNs in the presence of a rhodium(I) catalyst to give the five- and six-membered β-enamino esters in good yield. An (oxa-π-allyl)rhodium(I) intermediate, formed by initial conjugate addition of an Ar-rhodium(I) species, undergoes a facile intramolecular addition to the cyano group to construct the carbocyclic skeletons.",

author = "Tomoya Miura and Tatsuro Harumashi and Masahiro Murakami",

year = "2007",

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doi = "10.1021/ol062882y",

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AU - Miura, Tomoya

AU - Harumashi, Tatsuro

AU - Murakami, Masahiro

PY - 2007/3/1

Y1 - 2007/3/1

N2 - (Chemical Equation Presented) Unsaturated esters possessing a pendent cyano moiety react with B-Ar-9-BBNs in the presence of a rhodium(I) catalyst to give the five- and six-membered β-enamino esters in good yield. An (oxa-π-allyl)rhodium(I) intermediate, formed by initial conjugate addition of an Ar-rhodium(I) species, undergoes a facile intramolecular addition to the cyano group to construct the carbocyclic skeletons.

AB - (Chemical Equation Presented) Unsaturated esters possessing a pendent cyano moiety react with B-Ar-9-BBNs in the presence of a rhodium(I) catalyst to give the five- and six-membered β-enamino esters in good yield. An (oxa-π-allyl)rhodium(I) intermediate, formed by initial conjugate addition of an Ar-rhodium(I) species, undergoes a facile intramolecular addition to the cyano group to construct the carbocyclic skeletons.

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Cyclization reaction of cyano-substituted unsaturated esters prompted by conjugate addition of organoborons

Abstract

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