Catalytic asymmetric construction of quaternary α-amino acid containing pyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides to α-aminoacrylates

Zheng Wang; Shuai Luo; Shoude Zhang; Wu Lin Yang; Yang Zi Liu; Honglin Li; Xiaoyan Luo; Wei Ping Deng

doi:10.1002/chem.201300204

Catalytic asymmetric construction of quaternary α-amino acid containing pyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides to α-aminoacrylates

Zheng Wang^*
, Shuai Luo
, Shoude Zhang
, Wu Lin Yang
, Yang Zi Liu
, Honglin Li
, Xiaoyan Luo
, Wei Ping Deng

^*Corresponding author for this work

East China University of Science and Technology

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

51 Scopus citations

Abstract

The first catalytic enantioselective 1,3-dipolar cycloaddition of azomethine ylides to α-aminoacrylate catalyzed by a AgOAc/ferrocenyl oxazolinylphosphine (FOXAP) system was developed, which exhibits excellent exo- and enantioselectivity (92-99 % ee). This process provides efficient access to useful 4-aminopyrrolidine-2,4-dicarboxylic acid (APDC)-like compounds containing a unique quaternary α-amino acid unit.

Original language	English
Pages (from-to)	6739-6745
Number of pages	7
Journal	Chemistry - A European Journal
Volume	19
Issue number	21
DOIs	https://doi.org/10.1002/chem.201300204
State	Published - 17 May 2013
Externally published	Yes

Keywords

asymmetric catalysis
azomethine ylides
cycloaddition
silver
α-amino acids

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10.1002/chem.201300204

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title = "Catalytic asymmetric construction of quaternary α-amino acid containing pyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides to α-aminoacrylates",

abstract = "The first catalytic enantioselective 1,3-dipolar cycloaddition of azomethine ylides to α-aminoacrylate catalyzed by a AgOAc/ferrocenyl oxazolinylphosphine (FOXAP) system was developed, which exhibits excellent exo- and enantioselectivity (92-99 \% ee). This process provides efficient access to useful 4-aminopyrrolidine-2,4-dicarboxylic acid (APDC)-like compounds containing a unique quaternary α-amino acid unit.",

keywords = "asymmetric catalysis, azomethine ylides, cycloaddition, silver, α-amino acids",

author = "Zheng Wang and Shuai Luo and Shoude Zhang and Yang, \{Wu Lin\} and Liu, \{Yang Zi\} and Honglin Li and Xiaoyan Luo and Deng, \{Wei Ping\}",

year = "2013",

month = may,

day = "17",

doi = "10.1002/chem.201300204",

language = "英语",

volume = "19",

pages = "6739--6745",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley and Sons Inc",

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TY - JOUR

T1 - Catalytic asymmetric construction of quaternary α-amino acid containing pyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides to α-aminoacrylates

AU - Wang, Zheng

AU - Luo, Shuai

AU - Zhang, Shoude

AU - Yang, Wu Lin

AU - Liu, Yang Zi

AU - Li, Honglin

AU - Luo, Xiaoyan

AU - Deng, Wei Ping

PY - 2013/5/17

Y1 - 2013/5/17

N2 - The first catalytic enantioselective 1,3-dipolar cycloaddition of azomethine ylides to α-aminoacrylate catalyzed by a AgOAc/ferrocenyl oxazolinylphosphine (FOXAP) system was developed, which exhibits excellent exo- and enantioselectivity (92-99 % ee). This process provides efficient access to useful 4-aminopyrrolidine-2,4-dicarboxylic acid (APDC)-like compounds containing a unique quaternary α-amino acid unit.

AB - The first catalytic enantioselective 1,3-dipolar cycloaddition of azomethine ylides to α-aminoacrylate catalyzed by a AgOAc/ferrocenyl oxazolinylphosphine (FOXAP) system was developed, which exhibits excellent exo- and enantioselectivity (92-99 % ee). This process provides efficient access to useful 4-aminopyrrolidine-2,4-dicarboxylic acid (APDC)-like compounds containing a unique quaternary α-amino acid unit.

KW - asymmetric catalysis

KW - azomethine ylides

KW - cycloaddition

KW - silver

KW - α-amino acids

UR - https://www.scopus.com/pages/publications/84877775101

U2 - 10.1002/chem.201300204

DO - 10.1002/chem.201300204

M3 - 文章

C2 - 23553867

AN - SCOPUS:84877775101

SN - 0947-6539

VL - 19

SP - 6739

EP - 6745

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 21

ER -

Catalytic asymmetric construction of quaternary α-amino acid containing pyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides to α-aminoacrylates

Abstract

Keywords

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