One-pot diastereoselective synthesis of tetrahydroepimino-benzo[b]azocines through sequential [3+2]-cycloaddition and Staudinger-aza-Wittig reactions

Xiaoming Ma; Xiaofeng Zhang; Guoshu Xie; John Mark Awad; Wei Zhang

doi:10.1016/j.tetlet.2019.151127

One-pot diastereoselective synthesis of tetrahydroepimino-benzo[b]azocines through sequential [3+2]-cycloaddition and Staudinger-aza-Wittig reactions

Xiaoming Ma
, Xiaofeng Zhang
, Guoshu Xie
, John Mark Awad
, Wei Zhang

Chemistry

Changzhou University
University of Massachusetts Boston
Harvard University

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

Abstract

The one-pot synthesis of tetrahydro-epiminobenzo[b]azocines through a sequential 1,3-dipolar cycloaddition and intramolecular Staudinger-aza-Wittig reaction sequence is reported. This methodology provides a new and efficient approach for medium-sized and bridged nitrogen heterocyclic molecules.

Original language	English
Article number	151127
Journal	Tetrahedron Letters
Volume	60
Issue number	40
DOIs	https://doi.org/10.1016/j.tetlet.2019.151127
State	Published - Oct 3 2019

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Aza-Wittig reaction
One-pot synthesis
Tetrahydroepimino-benzo[b]azocine
[3+2] Cycloaddition

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10.1016/j.tetlet.2019.151127

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title = "One-pot diastereoselective synthesis of tetrahydroepimino-benzo[b]azocines through sequential [3+2]-cycloaddition and Staudinger-aza-Wittig reactions",

abstract = "The one-pot synthesis of tetrahydro-epiminobenzo[b]azocines through a sequential 1,3-dipolar cycloaddition and intramolecular Staudinger-aza-Wittig reaction sequence is reported. This methodology provides a new and efficient approach for medium-sized and bridged nitrogen heterocyclic molecules.",

keywords = "Aza-Wittig reaction, One-pot synthesis, Tetrahydroepimino-benzo[b]azocine, [3+2] Cycloaddition",

author = "Xiaoming Ma and Xiaofeng Zhang and Guoshu Xie and Awad, \{John Mark\} and Wei Zhang",

note = "Publisher Copyright: {\textcopyright} 2019 Elsevier Ltd",

year = "2019",

month = oct,

day = "3",

doi = "10.1016/j.tetlet.2019.151127",

language = "English",

volume = "60",

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TY - JOUR

T1 - One-pot diastereoselective synthesis of tetrahydroepimino-benzo[b]azocines through sequential [3+2]-cycloaddition and Staudinger-aza-Wittig reactions

AU - Ma, Xiaoming

AU - Zhang, Xiaofeng

AU - Xie, Guoshu

AU - Awad, John Mark

AU - Zhang, Wei

PY - 2019/10/3

Y1 - 2019/10/3

N2 - The one-pot synthesis of tetrahydro-epiminobenzo[b]azocines through a sequential 1,3-dipolar cycloaddition and intramolecular Staudinger-aza-Wittig reaction sequence is reported. This methodology provides a new and efficient approach for medium-sized and bridged nitrogen heterocyclic molecules.

AB - The one-pot synthesis of tetrahydro-epiminobenzo[b]azocines through a sequential 1,3-dipolar cycloaddition and intramolecular Staudinger-aza-Wittig reaction sequence is reported. This methodology provides a new and efficient approach for medium-sized and bridged nitrogen heterocyclic molecules.

KW - Aza-Wittig reaction

KW - One-pot synthesis

KW - Tetrahydroepimino-benzo[b]azocine

KW - [3+2] Cycloaddition

UR - https://www.scopus.com/pages/publications/85072068508

UR - https://www.scopus.com/pages/publications/85072068508#tab=citedBy

U2 - 10.1016/j.tetlet.2019.151127

DO - 10.1016/j.tetlet.2019.151127

M3 - Article

AN - SCOPUS:85072068508

SN - 0040-4039

VL - 60

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 40

M1 - 151127

ER -

One-pot diastereoselective synthesis of tetrahydroepimino-benzo[b]azocines through sequential [3+2]-cycloaddition and Staudinger-aza-Wittig reactions

Abstract

ASJC Scopus Subject Areas

Keywords

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