Gold-catalyzed dearomative spirocyclization of aryl alkynoate esters

Mark D. Aparece; Paul A. Vadola

doi:10.1021/ol503022h

Gold-catalyzed dearomative spirocyclization of aryl alkynoate esters

Mark D. Aparece, Paul A. Vadola^*

^*Corresponding author for this work

Chemistry

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

69 Scopus citations

Abstract

Aryl alkynoate esters undergo gold-catalyzed spirocyclization under mild conditions, affording spirolactones in high yields. This approach obviates the need for stoichiometric halogenating reagents typically employed for alkyne activation in related transformations. Water was found to play a critical role in governing the product selectivity. Anhydrous conditions lead selectively to coumarin products, as has previously been observed for aryl alkynoate esters, while the addition of 1 equiv of water leads selectively to spirocycle formation.

Original language	English (US)
Pages (from-to)	6008-6011
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	22
DOIs	https://doi.org/10.1021/ol503022h
State	Published - Nov 21 2014

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol503022h

Cite this

@article{06bbc25c64db4a3b80d5c7e35a06a7dc,

title = "Gold-catalyzed dearomative spirocyclization of aryl alkynoate esters",

abstract = "Aryl alkynoate esters undergo gold-catalyzed spirocyclization under mild conditions, affording spirolactones in high yields. This approach obviates the need for stoichiometric halogenating reagents typically employed for alkyne activation in related transformations. Water was found to play a critical role in governing the product selectivity. Anhydrous conditions lead selectively to coumarin products, as has previously been observed for aryl alkynoate esters, while the addition of 1 equiv of water leads selectively to spirocycle formation.",

author = "Aparece, {Mark D.} and Vadola, {Paul A.}",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2014",

month = nov,

day = "21",

doi = "10.1021/ol503022h",

language = "English (US)",

volume = "16",

pages = "6008--6011",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "22",

}

TY - JOUR

T1 - Gold-catalyzed dearomative spirocyclization of aryl alkynoate esters

AU - Aparece, Mark D.

AU - Vadola, Paul A.

PY - 2014/11/21

Y1 - 2014/11/21

N2 - Aryl alkynoate esters undergo gold-catalyzed spirocyclization under mild conditions, affording spirolactones in high yields. This approach obviates the need for stoichiometric halogenating reagents typically employed for alkyne activation in related transformations. Water was found to play a critical role in governing the product selectivity. Anhydrous conditions lead selectively to coumarin products, as has previously been observed for aryl alkynoate esters, while the addition of 1 equiv of water leads selectively to spirocycle formation.

AB - Aryl alkynoate esters undergo gold-catalyzed spirocyclization under mild conditions, affording spirolactones in high yields. This approach obviates the need for stoichiometric halogenating reagents typically employed for alkyne activation in related transformations. Water was found to play a critical role in governing the product selectivity. Anhydrous conditions lead selectively to coumarin products, as has previously been observed for aryl alkynoate esters, while the addition of 1 equiv of water leads selectively to spirocycle formation.

UR - http://www.scopus.com/inward/record.url?scp=84912550706&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84912550706&partnerID=8YFLogxK

U2 - 10.1021/ol503022h

DO - 10.1021/ol503022h

M3 - Article

C2 - 25365452

AN - SCOPUS:84912550706

VL - 16

SP - 6008

EP - 6011

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 22

ER -

Gold-catalyzed dearomative spirocyclization of aryl alkynoate esters

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this