Copper (II)/RuPHOX-Catalyzed Enantioselective Mannich-Type Reaction of Glycine Schiff Bases with Cyclic Ketimines

Qihang Shao; Liang Wu; Jianzhong Chen; Ilya D. Gridnev; Guoqiang Yang; Fang Xie; Wanbin Zhang

doi:10.1002/adsc.201800850

Copper (II)/RuPHOX-Catalyzed Enantioselective Mannich-Type Reaction of Glycine Schiff Bases with Cyclic Ketimines

Qihang Shao, Liang Wu, Jianzhong Chen, Ilya D. Gridnev, Guoqiang Yang, Fang Xie, Wanbin Zhang

SCI - Chemistry

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

23 Citations (Scopus)

Abstract

A Cu(II)/RuPHOX-catalyzed enantioselective Mannich-type reaction of glycine Schiff bases with cyclic ketimines was developed, affording chiral α,ß-diamino acid derivatives in good yields with moderate to good ee and dr values. This provides an efficient methodology for furnishing chiral C^β-tetrasubstituted α,β-diamino acid precursors. The catalytic system is compatible with a series of substrates. In addition, an interesting nonlinear effect of the catalyst's enantiomeric composition on reaction enantioselectivity was observed. (Figure presented.).

Original language	English
Pages (from-to)	4625-4633
Number of pages	9
Journal	Advanced Synthesis and Catalysis
Volume	360
Issue number	23
DOIs	https://doi.org/10.1002/adsc.201800850
Publication status	Published - 2018 Dec 3

Keywords

Cu
Mannich-type reaction
RuPHOX
asymmetric catalytic
cyclic ketimines

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201800850

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title = "Copper (II)/RuPHOX-Catalyzed Enantioselective Mannich-Type Reaction of Glycine Schiff Bases with Cyclic Ketimines",

abstract = "A Cu(II)/RuPHOX-catalyzed enantioselective Mannich-type reaction of glycine Schiff bases with cyclic ketimines was developed, affording chiral α,{\ss}-diamino acid derivatives in good yields with moderate to good ee and dr values. This provides an efficient methodology for furnishing chiral Cβ-tetrasubstituted α,β-diamino acid precursors. The catalytic system is compatible with a series of substrates. In addition, an interesting nonlinear effect of the catalyst's enantiomeric composition on reaction enantioselectivity was observed. (Figure presented.).",

keywords = "Cu, Mannich-type reaction, RuPHOX, asymmetric catalytic, cyclic ketimines",

author = "Qihang Shao and Liang Wu and Jianzhong Chen and Gridnev, {Ilya D.} and Guoqiang Yang and Fang Xie and Wanbin Zhang",

note = "Funding Information: The National Natural Science Foundation of China (Nos. 21572129, 21620102003, 21772119), and Shanghai Municipal Education Commission (No. 201701070002E00030) are acknowledged for financial support. The authors thank the Instrumental Analysis Center of SJTU. Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

month = dec,

day = "3",

doi = "10.1002/adsc.201800850",

language = "English",

volume = "360",

pages = "4625--4633",

journal = "Advanced Synthesis and Catalysis",

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TY - JOUR

T1 - Copper (II)/RuPHOX-Catalyzed Enantioselective Mannich-Type Reaction of Glycine Schiff Bases with Cyclic Ketimines

AU - Shao, Qihang

AU - Wu, Liang

AU - Chen, Jianzhong

AU - Gridnev, Ilya D.

AU - Yang, Guoqiang

AU - Xie, Fang

AU - Zhang, Wanbin

N1 - Funding Information: The National Natural Science Foundation of China (Nos. 21572129, 21620102003, 21772119), and Shanghai Municipal Education Commission (No. 201701070002E00030) are acknowledged for financial support. The authors thank the Instrumental Analysis Center of SJTU. Publisher Copyright: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/12/3

Y1 - 2018/12/3

N2 - A Cu(II)/RuPHOX-catalyzed enantioselective Mannich-type reaction of glycine Schiff bases with cyclic ketimines was developed, affording chiral α,ß-diamino acid derivatives in good yields with moderate to good ee and dr values. This provides an efficient methodology for furnishing chiral Cβ-tetrasubstituted α,β-diamino acid precursors. The catalytic system is compatible with a series of substrates. In addition, an interesting nonlinear effect of the catalyst's enantiomeric composition on reaction enantioselectivity was observed. (Figure presented.).

AB - A Cu(II)/RuPHOX-catalyzed enantioselective Mannich-type reaction of glycine Schiff bases with cyclic ketimines was developed, affording chiral α,ß-diamino acid derivatives in good yields with moderate to good ee and dr values. This provides an efficient methodology for furnishing chiral Cβ-tetrasubstituted α,β-diamino acid precursors. The catalytic system is compatible with a series of substrates. In addition, an interesting nonlinear effect of the catalyst's enantiomeric composition on reaction enantioselectivity was observed. (Figure presented.).

KW - Cu

KW - Mannich-type reaction

KW - RuPHOX

KW - asymmetric catalytic

KW - cyclic ketimines

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U2 - 10.1002/adsc.201800850

DO - 10.1002/adsc.201800850

M3 - Article

AN - SCOPUS:85055948506

SN - 1615-4150

VL - 360

SP - 4625

EP - 4633

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 23

ER -

Copper (II)/RuPHOX-Catalyzed Enantioselective Mannich-Type Reaction of Glycine Schiff Bases with Cyclic Ketimines

Abstract

Keywords

ASJC Scopus subject areas

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