The copper-catalyzed asymmetric construction of a dispiropyrrolidine skeleton via 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides

Wu-Lin Yang; Yang-Zi Liu; Shuai Luo; Xingxin Yu; John S Fossey; Wei-Ping Deng

doi:10.1039/c5cc02362a

The copper-catalyzed asymmetric construction of a dispiropyrrolidine skeleton via 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides

Wu-Lin Yang
, Yang-Zi Liu
, Shuai Luo
, Xingxin Yu
, John S Fossey
, Wei-Ping Deng

Chemistry

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

48 Citations (Scopus)

Abstract

A highly efficient asymmetric 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides catalyzed by a novel chiral N,O-ligand/Cu(OAc)2 system is reported, affording dispiropyrrolidine derivatives with spiro quaternary stereogenic centers in good to excellent yields (up to 90%), excellent levels of diastereoselectivities (>20 : 1 dr) and enantioselectivities (up to 97% ee).

Original language	English
Pages (from-to)	9212-9215
Number of pages	4
Journal	Chemical Communications
Volume	51
Issue number	44
Early online date	28 Apr 2015
DOIs	https://doi.org/10.1039/c5cc02362a
Publication status	Published - 19 May 2015

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title = "The copper-catalyzed asymmetric construction of a dispiropyrrolidine skeleton via 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides",

abstract = "A highly efficient asymmetric 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides catalyzed by a novel chiral N,O-ligand/Cu(OAc)2 system is reported, affording dispiropyrrolidine derivatives with spiro quaternary stereogenic centers in good to excellent yields (up to 90\%), excellent levels of diastereoselectivities (>20 : 1 dr) and enantioselectivities (up to 97\% ee).",

author = "Wu-Lin Yang and Yang-Zi Liu and Shuai Luo and Xingxin Yu and Fossey, \{John S\} and Wei-Ping Deng",

year = "2015",

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T1 - The copper-catalyzed asymmetric construction of a dispiropyrrolidine skeleton via 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides

AU - Yang, Wu-Lin

AU - Liu, Yang-Zi

AU - Luo, Shuai

AU - Yu, Xingxin

AU - Fossey, John S

AU - Deng, Wei-Ping

PY - 2015/5/19

Y1 - 2015/5/19

N2 - A highly efficient asymmetric 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides catalyzed by a novel chiral N,O-ligand/Cu(OAc)2 system is reported, affording dispiropyrrolidine derivatives with spiro quaternary stereogenic centers in good to excellent yields (up to 90%), excellent levels of diastereoselectivities (>20 : 1 dr) and enantioselectivities (up to 97% ee).

AB - A highly efficient asymmetric 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides catalyzed by a novel chiral N,O-ligand/Cu(OAc)2 system is reported, affording dispiropyrrolidine derivatives with spiro quaternary stereogenic centers in good to excellent yields (up to 90%), excellent levels of diastereoselectivities (>20 : 1 dr) and enantioselectivities (up to 97% ee).

U2 - 10.1039/c5cc02362a

DO - 10.1039/c5cc02362a

M3 - Article

C2 - 25952504

SN - 1359-7345

VL - 51

SP - 9212

EP - 9215

JO - Chemical Communications

JF - Chemical Communications

IS - 44

ER -

The copper-catalyzed asymmetric construction of a dispiropyrrolidine skeleton via 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides

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