An Approach to the Efficient Syntheses of Chiral Phosphino-Carboxylic Acid Esters

Renta Jonathan Chew; Kristel Sepp; Bin-Bin Li; Yongxin Li; Peng-Cheng Zhu; Nguan Soon Tan; Pak-Hing Leung

doi:10.1002/adsc.201500638

An Approach to the Efficient Syntheses of Chiral Phosphino-Carboxylic Acid Esters

Renta Jonathan Chew, Kristel Sepp, Bin-Bin Li, Yongxin Li, Peng-Cheng Zhu, Nguan Soon Tan, Pak-Hing Leung^*

^*Corresponding author for this work

School of Chemistry

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

Abstract

The catalytic hydrophosphination reaction is one of the most sustainable chemical transformations today. Here, the palladium-catalyzed asymmetric P-H addition of diarylphosphines with and analogues is described. Chiral phosphine products are obtained in 100% atom economy and without cumbersome protection-de-protection manipulations. The obtained products can be subsequently transformed to bear various functionalities, including phosphino-carboxylic esters which play critical roles in catalysis and as synthetic aids. Anti-tumour activities of the corresponding gold-phosphine complexes have been explored, contributing to existing chemotherapeutic research in cancer treatment.

Original language	English
Pages (from-to)	3297-3302
Number of pages	6
Journal	Advanced Synthesis & Catalysis
Volume	357
Issue number	14-15
DOIs	https://doi.org/10.1002/adsc.201500638
Publication status	Published - 12 Oct 2015

Keywords / Materials (for Non-textual outputs)

asymmetric catalysis
benzotriazoles
hydrophosphination
palladium
phospha-Michael reaction
N-ACYLBENZOTRIAZOLES
BREAST-CANCER
OXIDES
DERIVATIVES
COMPLEXES
LIGANDS
DIARYLPHOSPHINES
CISPLATIN
ACCESS
DIPHENYLPHOSPHINE

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10.1002/adsc.201500638

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title = "An Approach to the Efficient Syntheses of Chiral Phosphino-Carboxylic Acid Esters",

abstract = "The catalytic hydrophosphination reaction is one of the most sustainable chemical transformations today. Here, the palladium-catalyzed asymmetric P-H addition of diarylphosphines with and analogues is described. Chiral phosphine products are obtained in 100% atom economy and without cumbersome protection-de-protection manipulations. The obtained products can be subsequently transformed to bear various functionalities, including phosphino-carboxylic esters which play critical roles in catalysis and as synthetic aids. Anti-tumour activities of the corresponding gold-phosphine complexes have been explored, contributing to existing chemotherapeutic research in cancer treatment.",

keywords = "asymmetric catalysis, benzotriazoles, hydrophosphination, palladium, phospha-Michael reaction, N-ACYLBENZOTRIAZOLES, BREAST-CANCER, OXIDES, DERIVATIVES, COMPLEXES, LIGANDS, DIARYLPHOSPHINES, CISPLATIN, ACCESS, DIPHENYLPHOSPHINE",

author = "Chew, {Renta Jonathan} and Kristel Sepp and Bin-Bin Li and Yongxin Li and Peng-Cheng Zhu and Tan, {Nguan Soon} and Pak-Hing Leung",

year = "2015",

month = oct,

day = "12",

doi = "10.1002/adsc.201500638",

language = "English",

volume = "357",

pages = "3297--3302",

journal = "Advanced Synthesis & Catalysis",

issn = "1615-4150",

publisher = "Wiley",

number = "14-15",

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TY - JOUR

T1 - An Approach to the Efficient Syntheses of Chiral Phosphino-Carboxylic Acid Esters

AU - Chew, Renta Jonathan

AU - Sepp, Kristel

AU - Li, Bin-Bin

AU - Li, Yongxin

AU - Zhu, Peng-Cheng

AU - Tan, Nguan Soon

AU - Leung, Pak-Hing

PY - 2015/10/12

Y1 - 2015/10/12

N2 - The catalytic hydrophosphination reaction is one of the most sustainable chemical transformations today. Here, the palladium-catalyzed asymmetric P-H addition of diarylphosphines with and analogues is described. Chiral phosphine products are obtained in 100% atom economy and without cumbersome protection-de-protection manipulations. The obtained products can be subsequently transformed to bear various functionalities, including phosphino-carboxylic esters which play critical roles in catalysis and as synthetic aids. Anti-tumour activities of the corresponding gold-phosphine complexes have been explored, contributing to existing chemotherapeutic research in cancer treatment.

AB - The catalytic hydrophosphination reaction is one of the most sustainable chemical transformations today. Here, the palladium-catalyzed asymmetric P-H addition of diarylphosphines with and analogues is described. Chiral phosphine products are obtained in 100% atom economy and without cumbersome protection-de-protection manipulations. The obtained products can be subsequently transformed to bear various functionalities, including phosphino-carboxylic esters which play critical roles in catalysis and as synthetic aids. Anti-tumour activities of the corresponding gold-phosphine complexes have been explored, contributing to existing chemotherapeutic research in cancer treatment.

KW - asymmetric catalysis

KW - benzotriazoles

KW - hydrophosphination

KW - palladium

KW - phospha-Michael reaction

KW - N-ACYLBENZOTRIAZOLES

KW - BREAST-CANCER

KW - OXIDES

KW - DERIVATIVES

KW - COMPLEXES

KW - LIGANDS

KW - DIARYLPHOSPHINES

KW - CISPLATIN

KW - ACCESS

KW - DIPHENYLPHOSPHINE

U2 - 10.1002/adsc.201500638

DO - 10.1002/adsc.201500638

M3 - Article

SN - 1615-4150

VL - 357

SP - 3297

EP - 3302

JO - Advanced Synthesis & Catalysis

JF - Advanced Synthesis & Catalysis

IS - 14-15

ER -

An Approach to the Efficient Syntheses of Chiral Phosphino-Carboxylic Acid Esters

Abstract

Keywords / Materials (for Non-textual outputs)

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