Gold-catalyzed intramolecular hydroalkoxylation/cyclization of conjugated dienyl alcohols

B. Chandrasekhar; Jae Sang Ryu

doi:10.1016/j.tet.2012.03.120

Gold-catalyzed intramolecular hydroalkoxylation/cyclization of conjugated dienyl alcohols

B. Chandrasekhar, Jae Sang Ryu

Pharmaceutical Sciences

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

7 Scopus citations

Abstract

Catalytic intramolecular additions of hydroxyl groups to tethered conjugated dienes are described. The reactions proceed smoothly at 60 °C in the presence of 5 mol % of (PPh ₃)AuCl/AgOTf as a catalyst. A broad range of structurally diverse conjugated dienes produce substituted tetrahydrofurans and tetrahydropyrans in good yields. This reaction represents an atom-economic route to construct five- and six-membered cyclic ethers.

Original language	English
Pages (from-to)	4805-4812
Number of pages	8
Journal	Tetrahedron
Volume	68
Issue number	24
DOIs	https://doi.org/10.1016/j.tet.2012.03.120
State	Published - 17 Jun 2012

Bibliographical note

Funding Information:
This work was supported by the grant from the National Core Research Center Program (No. 2012-0000952 ) of the Ministry of Science & Technology and by the Ewha Global Top5 Grant 2011 of Ewha Womans University .

Keywords

Alcohol
Conjugated diene
Cyclization
Gold
Hydroalkoxylation

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title = "Gold-catalyzed intramolecular hydroalkoxylation/cyclization of conjugated dienyl alcohols",

abstract = "Catalytic intramolecular additions of hydroxyl groups to tethered conjugated dienes are described. The reactions proceed smoothly at 60 °C in the presence of 5 mol % of (PPh 3)AuCl/AgOTf as a catalyst. A broad range of structurally diverse conjugated dienes produce substituted tetrahydrofurans and tetrahydropyrans in good yields. This reaction represents an atom-economic route to construct five- and six-membered cyclic ethers.",

keywords = "Alcohol, Conjugated diene, Cyclization, Gold, Hydroalkoxylation",

author = "B. Chandrasekhar and Ryu, {Jae Sang}",

note = "Funding Information: This work was supported by the grant from the National Core Research Center Program (No. 2012-0000952 ) of the Ministry of Science & Technology and by the Ewha Global Top5 Grant 2011 of Ewha Womans University . ",

year = "2012",

month = jun,

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doi = "10.1016/j.tet.2012.03.120",

language = "English",

volume = "68",

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journal = "Tetrahedron",

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T1 - Gold-catalyzed intramolecular hydroalkoxylation/cyclization of conjugated dienyl alcohols

AU - Chandrasekhar, B.

AU - Ryu, Jae Sang

N1 - Funding Information: This work was supported by the grant from the National Core Research Center Program (No. 2012-0000952 ) of the Ministry of Science & Technology and by the Ewha Global Top5 Grant 2011 of Ewha Womans University .

PY - 2012/6/17

Y1 - 2012/6/17

N2 - Catalytic intramolecular additions of hydroxyl groups to tethered conjugated dienes are described. The reactions proceed smoothly at 60 °C in the presence of 5 mol % of (PPh 3)AuCl/AgOTf as a catalyst. A broad range of structurally diverse conjugated dienes produce substituted tetrahydrofurans and tetrahydropyrans in good yields. This reaction represents an atom-economic route to construct five- and six-membered cyclic ethers.

AB - Catalytic intramolecular additions of hydroxyl groups to tethered conjugated dienes are described. The reactions proceed smoothly at 60 °C in the presence of 5 mol % of (PPh 3)AuCl/AgOTf as a catalyst. A broad range of structurally diverse conjugated dienes produce substituted tetrahydrofurans and tetrahydropyrans in good yields. This reaction represents an atom-economic route to construct five- and six-membered cyclic ethers.

KW - Alcohol

KW - Conjugated diene

KW - Cyclization

KW - Gold

KW - Hydroalkoxylation

UR - http://www.scopus.com/inward/record.url?scp=84861221977&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2012.03.120

DO - 10.1016/j.tet.2012.03.120

M3 - Article

AN - SCOPUS:84861221977

SN - 0040-4020

VL - 68

SP - 4805

EP - 4812

JO - Tetrahedron

JF - Tetrahedron

IS - 24

ER -

Gold-catalyzed intramolecular hydroalkoxylation/cyclization of conjugated dienyl alcohols

Abstract

Bibliographical note

Keywords

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