Intramolecular (4 + 3) cycloadditions of nitrogen-tethered epoxy enosilanes for the synthesis of heteropolycycles

Jiayun He; Shuk Mei Lam; Jerome P.L. Ng; Wing Tak Wong; Pauline Chiu

doi:10.1016/j.cclet.2019.04.051

Intramolecular (4 + 3) cycloadditions of nitrogen-tethered epoxy enosilanes for the synthesis of heteropolycycles

Jiayun He, Shuk Mei Lam, Jerome P.L. Ng, Wing Tak Wong, Pauline Chiu

Research output: Journal article publication › Journal article › Academic research › peer-review

1 Citation (Scopus)

Abstract

Furans bearing epoxy enolsilane units via a tether that incorporates a nitrogen heteroatom, undergo intramolecular (4 + 3) cycloadditions to generate bis-heteroatomic polycyclic adducts having piperidine moieties in their frameworks. The cycloadducts, ultimately derived from furfural, a renewal chemical feedstock, are obtained with up to 4:1 dr and with ee retained from the epoxide.

Original language	English
Pages (from-to)	1523-1526
Number of pages	4
Journal	Chinese Chemical Letters
Volume	30
Issue number	8
DOIs	https://doi.org/10.1016/j.cclet.2019.04.051
Publication status	Published - Aug 2019

Keywords

(4 + 3) cycloaddition
Epoxides
Furan
Heterocycles
Intramolecular
Piperidine
Polycyclic compounds

ASJC Scopus subject areas

General Chemistry

More information

10.1016/j.cclet.2019.04.051

http://hdl.handle.net/10397/101515

Cite this

@article{7f6713b19b074248bcf764babda18eee,

title = "Intramolecular (4 + 3) cycloadditions of nitrogen-tethered epoxy enosilanes for the synthesis of heteropolycycles",

abstract = "Furans bearing epoxy enolsilane units via a tether that incorporates a nitrogen heteroatom, undergo intramolecular (4 + 3) cycloadditions to generate bis-heteroatomic polycyclic adducts having piperidine moieties in their frameworks. The cycloadducts, ultimately derived from furfural, a renewal chemical feedstock, are obtained with up to 4:1 dr and with ee retained from the epoxide.",

keywords = "(4 + 3) cycloaddition, Epoxides, Furan, Heterocycles, Intramolecular, Piperidine, Polycyclic compounds",

author = "Jiayun He and Lam, {Shuk Mei} and Ng, {Jerome P.L.} and Wong, {Wing Tak} and Pauline Chiu",

year = "2019",

month = aug,

doi = "10.1016/j.cclet.2019.04.051",

language = "English",

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journal = "Chinese Chemical Letters",

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T1 - Intramolecular (4 + 3) cycloadditions of nitrogen-tethered epoxy enosilanes for the synthesis of heteropolycycles

AU - He, Jiayun

AU - Lam, Shuk Mei

AU - Ng, Jerome P.L.

AU - Wong, Wing Tak

AU - Chiu, Pauline

PY - 2019/8

Y1 - 2019/8

N2 - Furans bearing epoxy enolsilane units via a tether that incorporates a nitrogen heteroatom, undergo intramolecular (4 + 3) cycloadditions to generate bis-heteroatomic polycyclic adducts having piperidine moieties in their frameworks. The cycloadducts, ultimately derived from furfural, a renewal chemical feedstock, are obtained with up to 4:1 dr and with ee retained from the epoxide.

AB - Furans bearing epoxy enolsilane units via a tether that incorporates a nitrogen heteroatom, undergo intramolecular (4 + 3) cycloadditions to generate bis-heteroatomic polycyclic adducts having piperidine moieties in their frameworks. The cycloadducts, ultimately derived from furfural, a renewal chemical feedstock, are obtained with up to 4:1 dr and with ee retained from the epoxide.

KW - (4 + 3) cycloaddition

KW - Epoxides

KW - Furan

KW - Heterocycles

KW - Intramolecular

KW - Piperidine

KW - Polycyclic compounds

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U2 - 10.1016/j.cclet.2019.04.051

DO - 10.1016/j.cclet.2019.04.051

M3 - Journal article

AN - SCOPUS:85065236399

SN - 1001-8417

VL - 30

SP - 1523

EP - 1526

JO - Chinese Chemical Letters

JF - Chinese Chemical Letters

IS - 8

ER -