Sequential [3 + 2] and [4 + 2] cycloadditions for stereoselective synthesis of a novel polyheterocyclic scaffold

Qing Lu; Xin Huang; Gonghua Song; Chung Ming Sun; Jerry P. Jasinski; Amanda C. Keeley; Wei Zhang

doi:10.1021/co400026s

Sequential [3 + 2] and [4 + 2] cycloadditions for stereoselective synthesis of a novel polyheterocyclic scaffold

Qing Lu
, Xin Huang
, Gonghua Song
, Chung Ming Sun
, Jerry P. Jasinski
, Amanda C. Keeley
, Wei Zhang

Chemistry

University of Massachusetts Boston
East China University of Science and Technology
National Yang Ming Chiao Tung University
Keene State College

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

Abstract

A strategy of combining [3 + 2] cycloaddition and intramolecular Diels-Alder reaction is developed for the synthesis of a novel polycyclic scaffold with skeletal and substitutional diversities. Intermediates generated from stereoselective [3 + 2] cycloaddition of azomethine ylides and maleimides were derivatized for intramolecular Diels-Alder reaction of furan to form highly condensed heterocyclic products as racemic single diastereomers.

Original language	English
Pages (from-to)	350-355
Number of pages	6
Journal	ACS Combinatorial Science
Volume	15
Issue number	7
DOIs	https://doi.org/10.1021/co400026s
State	Published - Jul 8 2013

ASJC Scopus Subject Areas

General Chemistry

Keywords

[3 + 2] cycloaddition
intramolecular Diels-Alder reaction
polyheterocyclic scaffold
sequential cycloadditions
stereoselective annulation

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10.1021/co400026s

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abstract = "A strategy of combining [3 + 2] cycloaddition and intramolecular Diels-Alder reaction is developed for the synthesis of a novel polycyclic scaffold with skeletal and substitutional diversities. Intermediates generated from stereoselective [3 + 2] cycloaddition of azomethine ylides and maleimides were derivatized for intramolecular Diels-Alder reaction of furan to form highly condensed heterocyclic products as racemic single diastereomers.",

keywords = "[3 + 2] cycloaddition, intramolecular Diels-Alder reaction, polyheterocyclic scaffold, sequential cycloadditions, stereoselective annulation",

author = "Qing Lu and Xin Huang and Gonghua Song and Sun, \{Chung Ming\} and Jasinski, \{Jerry P.\} and Keeley, \{Amanda C.\} and Wei Zhang",

year = "2013",

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doi = "10.1021/co400026s",

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AU - Lu, Qing

AU - Huang, Xin

AU - Song, Gonghua

AU - Sun, Chung Ming

AU - Jasinski, Jerry P.

AU - Keeley, Amanda C.

AU - Zhang, Wei

PY - 2013/7/8

Y1 - 2013/7/8

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AB - A strategy of combining [3 + 2] cycloaddition and intramolecular Diels-Alder reaction is developed for the synthesis of a novel polycyclic scaffold with skeletal and substitutional diversities. Intermediates generated from stereoselective [3 + 2] cycloaddition of azomethine ylides and maleimides were derivatized for intramolecular Diels-Alder reaction of furan to form highly condensed heterocyclic products as racemic single diastereomers.

KW - [3 + 2] cycloaddition

KW - intramolecular Diels-Alder reaction

KW - polyheterocyclic scaffold

KW - sequential cycloadditions

KW - stereoselective annulation

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Sequential [3 + 2] and [4 + 2] cycloadditions for stereoselective synthesis of a novel polyheterocyclic scaffold

Abstract

ASJC Scopus Subject Areas

Keywords

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