Double [3 + 2] cycloadditions for diastereoselective synthesis of spirooxindole pyrrolizidines

Xiaofeng Zhang; Xiaoming Ma; Weiqi Qiu; Johnmark Awad; Wei Zhang

doi:10.1515/gps-2022-0088

Double [3 + 2] cycloadditions for diastereoselective synthesis of spirooxindole pyrrolizidines

Xiaofeng Zhang
, Xiaoming Ma
, Weiqi Qiu
, Johnmark Awad
, Wei Zhang

Chemistry

University of Massachusetts Boston
Harvard University
Broad Institute
Changzhou University

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

Abstract

One-pot two sequential [3 + 2] cycloadditions of azomethine ylides with different dipolarophiles for diastereoselective synthesis of spirooxindole pyrrolizidines are introduced. This one-pot synthesis involving five components generates a highly condensed ring system bearing seven stereocenters diastereoselectively. The new method has high pot, atom, and step economy. Only two equivalents of water are released as a side product.

Original language	English
Pages (from-to)	1128-1135
Number of pages	8
Journal	Green Processing and Synthesis
Volume	11
Issue number	1
DOIs	https://doi.org/10.1515/gps-2022-0088
State	Published - Jan 1 2022

ASJC Scopus Subject Areas

Environmental Chemistry
General Chemical Engineering
Renewable Energy, Sustainability and the Environment
Fuel Technology
Industrial and Manufacturing Engineering
Health, Toxicology and Mutagenesis

Keywords

1,3-dipolar
azomethine ylides
double [3 + 2] cycloaddition
one-pot
pyrrolizidines

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10.1515/gps-2022-0088

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abstract = "One-pot two sequential [3 + 2] cycloadditions of azomethine ylides with different dipolarophiles for diastereoselective synthesis of spirooxindole pyrrolizidines are introduced. This one-pot synthesis involving five components generates a highly condensed ring system bearing seven stereocenters diastereoselectively. The new method has high pot, atom, and step economy. Only two equivalents of water are released as a side product.",

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AU - Zhang, Xiaofeng

AU - Ma, Xiaoming

AU - Qiu, Weiqi

AU - Awad, Johnmark

AU - Zhang, Wei

PY - 2022/1/1

Y1 - 2022/1/1

N2 - One-pot two sequential [3 + 2] cycloadditions of azomethine ylides with different dipolarophiles for diastereoselective synthesis of spirooxindole pyrrolizidines are introduced. This one-pot synthesis involving five components generates a highly condensed ring system bearing seven stereocenters diastereoselectively. The new method has high pot, atom, and step economy. Only two equivalents of water are released as a side product.

AB - One-pot two sequential [3 + 2] cycloadditions of azomethine ylides with different dipolarophiles for diastereoselective synthesis of spirooxindole pyrrolizidines are introduced. This one-pot synthesis involving five components generates a highly condensed ring system bearing seven stereocenters diastereoselectively. The new method has high pot, atom, and step economy. Only two equivalents of water are released as a side product.

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KW - azomethine ylides

KW - double [3 + 2] cycloaddition

KW - one-pot

KW - pyrrolizidines

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JO - Green Processing and Synthesis

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IS - 1

ER -

Double [3 + 2] cycloadditions for diastereoselective synthesis of spirooxindole pyrrolizidines

Abstract

ASJC Scopus Subject Areas

Keywords

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