(4 + 3) cycloadditions of allenyl ether-derived oxygen-stabilized oxyallyls with furans

Xian Huang; Waygen Thor; Xiangyu Feng; Liangliang Kang; Min Yang; Chi Sing Lee; Yuen Kit Cheng; Shuzhong He

doi:10.1039/c9qo01349k

(4 + 3) cycloadditions of allenyl ether-derived oxygen-stabilized oxyallyls with furans

Xian Huang
, Waygen Thor
, Xiangyu Feng
, Liangliang Kang
, Min Yang
, Chi Sing Lee^*
, Yuen Kit Cheng^*
, Shuzhong He^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

11 Citations (Scopus)

Abstract

(4 + 3) cycloadditions between allenyl ethers and furans are described. The reaction features an in situ formation of oxygen-stabilized oxyallyls via epoxidations of allenyl ethers in the presence of H₂PO₄^-. The multiple interactions between the oxygen-stabilized oxyallyl species and H₂PO₄^- were studied using DFT calculations for rationalization of the regio- and diastereoselectivity of this cycloaddition. The utilities of this cycloaddition have been demonstrated by converting the (4 + 3) cycloadduct into the cyclohepta[b]benzofuran skeleton of frondosin B in two steps.

Original language	English
Pages (from-to)	255-260
Number of pages	6
Journal	Organic Chemistry Frontiers
Volume	7
Issue number	2
DOIs	https://doi.org/10.1039/c9qo01349k
Publication status	Published - 21 Jan 2020

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@article{02fa3d028cc24bbf92385a3c500f79d7,

title = "(4 + 3) cycloadditions of allenyl ether-derived oxygen-stabilized oxyallyls with furans",

abstract = "(4 + 3) cycloadditions between allenyl ethers and furans are described. The reaction features an in situ formation of oxygen-stabilized oxyallyls via epoxidations of allenyl ethers in the presence of H2PO4-. The multiple interactions between the oxygen-stabilized oxyallyl species and H2PO4- were studied using DFT calculations for rationalization of the regio- and diastereoselectivity of this cycloaddition. The utilities of this cycloaddition have been demonstrated by converting the (4 + 3) cycloadduct into the cyclohepta[b]benzofuran skeleton of frondosin B in two steps.",

author = "Xian Huang and Waygen Thor and Xiangyu Feng and Liangliang Kang and Min Yang and Lee, \{Chi Sing\} and Cheng, \{Yuen Kit\} and Shuzhong He",

note = "Funding Information: We thank the National Natural Science Foundation of China (Grant No. 21562011, 21861010 and 21871017), the Science and Technology Foundation of Guizhou Province (Qian Ke He J Zi [2015]2047, Qian Ke He platform talents [2018]5781), the Case Base Construction Project for Guizhou Graduate Education (KCALK2017012), Guizhou University Talent Project (No. [2014]36) and Hong Kong Baptist University (RC-SGT2/18-19/SCI/005 and RC-ICRS-18-19-01A) for their financial support.",

year = "2020",

month = jan,

day = "21",

doi = "10.1039/c9qo01349k",

language = "English",

volume = "7",

pages = "255--260",

journal = "Organic Chemistry Frontiers",

issn = "2052-4110",

publisher = "Royal Society of Chemistry",

number = "2",

}

TY - JOUR

T1 - (4 + 3) cycloadditions of allenyl ether-derived oxygen-stabilized oxyallyls with furans

AU - Huang, Xian

AU - Thor, Waygen

AU - Feng, Xiangyu

AU - Kang, Liangliang

AU - Yang, Min

AU - Lee, Chi Sing

AU - Cheng, Yuen Kit

AU - He, Shuzhong

N1 - Funding Information: We thank the National Natural Science Foundation of China (Grant No. 21562011, 21861010 and 21871017), the Science and Technology Foundation of Guizhou Province (Qian Ke He J Zi [2015]2047, Qian Ke He platform talents [2018]5781), the Case Base Construction Project for Guizhou Graduate Education (KCALK2017012), Guizhou University Talent Project (No. [2014]36) and Hong Kong Baptist University (RC-SGT2/18-19/SCI/005 and RC-ICRS-18-19-01A) for their financial support.

PY - 2020/1/21

Y1 - 2020/1/21

N2 - (4 + 3) cycloadditions between allenyl ethers and furans are described. The reaction features an in situ formation of oxygen-stabilized oxyallyls via epoxidations of allenyl ethers in the presence of H2PO4-. The multiple interactions between the oxygen-stabilized oxyallyl species and H2PO4- were studied using DFT calculations for rationalization of the regio- and diastereoselectivity of this cycloaddition. The utilities of this cycloaddition have been demonstrated by converting the (4 + 3) cycloadduct into the cyclohepta[b]benzofuran skeleton of frondosin B in two steps.

AB - (4 + 3) cycloadditions between allenyl ethers and furans are described. The reaction features an in situ formation of oxygen-stabilized oxyallyls via epoxidations of allenyl ethers in the presence of H2PO4-. The multiple interactions between the oxygen-stabilized oxyallyl species and H2PO4- were studied using DFT calculations for rationalization of the regio- and diastereoselectivity of this cycloaddition. The utilities of this cycloaddition have been demonstrated by converting the (4 + 3) cycloadduct into the cyclohepta[b]benzofuran skeleton of frondosin B in two steps.

UR - https://www.scopus.com/pages/publications/85078408127

U2 - 10.1039/c9qo01349k

DO - 10.1039/c9qo01349k

M3 - Journal article

AN - SCOPUS:85078408127

SN - 2052-4110

VL - 7

SP - 255

EP - 260

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 2

ER -

(4 + 3) cycloadditions of allenyl ether-derived oxygen-stabilized oxyallyls with furans

Abstract

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