An ylide transformation of rhodium(I) Carbene: Enantioselective three-component reaction through trapping of rhodium(I)-associated ammonium ylides by β-nitroacrylates

Xiaochu Ma; Jun Jiang; Siying Lv; Wenfeng Yao; Yang Yang; Shunying Liu; Fei Xia; Wenhao Hu

doi:10.1002/anie.201407740

An ylide transformation of rhodium(I) Carbene: Enantioselective three-component reaction through trapping of rhodium(I)-associated ammonium ylides by β-nitroacrylates

Xiaochu Ma, Jun Jiang, Siying Lv, Wenfeng Yao, Yang Yang, Shunying Liu, Fei Xia, Wenhao Hu

School of Chemistry and Molecular Engineering

East China Normal University

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

98 Scopus citations

Abstract

The chiral Rh^I-diene-catalyzed asymmetric three-component reaction of aryldiazoacetates, aromatic amines, and β-nitroacrylates was achieved to obtain γ-nitro-α-amino-succinates in good yields and with high diastereo-and enantioselectivity. This reaction is proposed to proceed through the enantioselective trapping of Rh^I-associated ammonium ylides by nitroacrylates. This new transformation represents the first example of Rh^I-carbene-induced ylide transformation.

Original language	English
Pages (from-to)	13136-13139
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	48
DOIs	https://doi.org/10.1002/anie.201407740
State	Published - 24 Nov 2014

Keywords

Ammonium ylide
Carbenes
Multicomponent reactions
Rhodium
β-nitroacrylates

Access to Document

10.1002/anie.201407740

Cite this

@article{1f5beb7a5f53436a96672a7dde93f6c5,

title = "An ylide transformation of rhodium(I) Carbene: Enantioselective three-component reaction through trapping of rhodium(I)-associated ammonium ylides by β-nitroacrylates",

abstract = "The chiral RhI-diene-catalyzed asymmetric three-component reaction of aryldiazoacetates, aromatic amines, and β-nitroacrylates was achieved to obtain γ-nitro-α-amino-succinates in good yields and with high diastereo-and enantioselectivity. This reaction is proposed to proceed through the enantioselective trapping of RhI-associated ammonium ylides by nitroacrylates. This new transformation represents the first example of RhI-carbene-induced ylide transformation.",

keywords = "Ammonium ylide, Carbenes, Multicomponent reactions, Rhodium, β-nitroacrylates",

author = "Xiaochu Ma and Jun Jiang and Siying Lv and Wenfeng Yao and Yang Yang and Shunying Liu and Fei Xia and Wenhao Hu",

note = "Publisher Copyright: {\textcopyright} 2014 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim.",

year = "2014",

month = nov,

day = "24",

doi = "10.1002/anie.201407740",

language = "英语",

volume = "53",

pages = "13136--13139",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "48",

}

An ylide transformation of rhodium(I) Carbene: Enantioselective three-component reaction through trapping of rhodium(I)-associated ammonium ylides by β-nitroacrylates. / Ma, Xiaochu; Jiang, Jun; Lv, Siying et al.
In: Angewandte Chemie - International Edition, Vol. 53, No. 48, 24.11.2014, p. 13136-13139.

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

TY - JOUR

T1 - An ylide transformation of rhodium(I) Carbene

T2 - Enantioselective three-component reaction through trapping of rhodium(I)-associated ammonium ylides by β-nitroacrylates

AU - Ma, Xiaochu

AU - Jiang, Jun

AU - Lv, Siying

AU - Yao, Wenfeng

AU - Yang, Yang

AU - Liu, Shunying

AU - Xia, Fei

AU - Hu, Wenhao

PY - 2014/11/24

Y1 - 2014/11/24

N2 - The chiral RhI-diene-catalyzed asymmetric three-component reaction of aryldiazoacetates, aromatic amines, and β-nitroacrylates was achieved to obtain γ-nitro-α-amino-succinates in good yields and with high diastereo-and enantioselectivity. This reaction is proposed to proceed through the enantioselective trapping of RhI-associated ammonium ylides by nitroacrylates. This new transformation represents the first example of RhI-carbene-induced ylide transformation.

AB - The chiral RhI-diene-catalyzed asymmetric three-component reaction of aryldiazoacetates, aromatic amines, and β-nitroacrylates was achieved to obtain γ-nitro-α-amino-succinates in good yields and with high diastereo-and enantioselectivity. This reaction is proposed to proceed through the enantioselective trapping of RhI-associated ammonium ylides by nitroacrylates. This new transformation represents the first example of RhI-carbene-induced ylide transformation.

KW - Ammonium ylide

KW - Carbenes

KW - Multicomponent reactions

KW - Rhodium

KW - β-nitroacrylates

UR - https://www.scopus.com/pages/publications/84915751225

U2 - 10.1002/anie.201407740

DO - 10.1002/anie.201407740

M3 - 文章

C2 - 25284605

AN - SCOPUS:84915751225

SN - 1433-7851

VL - 53

SP - 13136

EP - 13139

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 48

ER -

An ylide transformation of rhodium(I) Carbene: Enantioselective three-component reaction through trapping of rhodium(I)-associated ammonium ylides by β-nitroacrylates

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this