Catalytic Asymmetric Diarylphosphine Addition to α-Diazoesters for the Synthesis of P-Stereogenic Phosphinates via P*-N Bond Formation

被引：29

作者：

Balazs, Laszlo B. ^{[1
]}

Huang, Yinhua ^{[2
]}

Khalikuzzaman, Jasmina B. ^{[1
]}

Li, Yongxin ^{[1
]}

Pullarkat, Sumod A. ^{[1
]}

Leung, Pak-Hing ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

[2] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 311121, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 22期

关键词：

D O I：

10.1021/acs.joc.0c00181

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric catalytic P-H addition of racemic secondary phosphines to electrophilic alpha-diazoesters via P*-N bond formation is disclosed for the first time. Interaction between the diazoester and the palladium catalyst resulted in the unusually enhanced electrophilic ability of the terminal nitrogen in the diazo functionality, as opposed to the commonly expected formation of a metal carbene by nitrogen elimination. Further derivatization of the generated phosphinic hydrazones provided access to enantioenriched P-stereogenic diarylphosphinates via a simple transformation.

引用

页码：14763 / 14771

页数：9

共 44 条

[1] Enantioselective Cu-Catalyzed Arylation of Secondary Phosphine Oxides with Diaryliodonium Salts toward the Synthesis of P-Chiral Phosphines [J].

Beaud, Rodolphe ;

Phipps, Robert J. ;

Gaunt, Matthew J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (40) :13183-13186

[2] General Strategy for the Synthesis of P-Stereogenic Compounds [J].

Berger, Olivier ;

Montchamp, Jean-Luc .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (43) :11377-11380

[3] Palladium-catalyzed asymmetric phosphination. Scope, mechanism, and origin of enantioselectivity [J].

Blank, Natalia F. ;

Moncarz, Jillian R. ;

Brunker, Tim J. ;

Scriban, Corina ;

Anderson, Brian J. ;

Amir, Omar ;

Glueck, David S. ;

Zakharov, Lev N. ;

Golen, James A. ;

Incarvito, Christopher D. ;

Rheingold, Arnold L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (21) :6847-6858

[4] Asymmetric catalytic synthesis of P-stereogenic phosphines via a nucleophilic ruthenium phosphido complex [J].

Chan, VS ;

Stewart, IC ;

Bergman, RG ;

Toste, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (09) :2786-2787

[5] Our Odyssey with Functionalized Chiral Phosphines: From Optical Resolution to Asymmetric Synthesis to Catalysis [J].

Chew, Renta Jonathan ;

Leung, Pak-Hing .

CHEMICAL RECORD, 2016, 16 (01) :141-158

[6] A NEW AND HIGHLY ENANTIOSELECTIVE SYNTHETIC ROUTE TO P-CHIRAL PHOSPHINES AND DIPHOSPHINES [J].

COREY, EJ ;

CHEN, ZL ;

TANOURY, GJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) :11000-11001

[7] Synthesis of diversely functionalised 2,2-disubstituted oxetanes: fragment motifs in new chemical space [J].

Davis, Owen A. ;

Croft, Rosemary A. ;

Bull, James A. .

CHEMICAL COMMUNICATIONS, 2015, 51 (84) :15446-15449

[8] Carbenes: Synthesis, properties, and organometallic chemistry [J].

de Fremont, Pierre ;

Marion, Nicolas ;

Nolan, Steven P. .

COORDINATION CHEMISTRY REVIEWS, 2009, 253 (7-8) :862-892

[9] Synthesis of P-stereogenic diarylphosphinic amides by directed lithiation: transformation into tertiary phosphine oxides via methanolysis, aryne chemistry and complexation behaviour toward zinc(II) [J].

del Aguila-Sanchez, Miguel A. ;

Navarro, Yolanda ;

Garcia Lopez, Jesus ;

Guedes, Guilherme P. ;

Lopez Ortiz, Fernando .

DALTON TRANSACTIONS, 2016, 45 (05) :2008-2022

[10]

Doyle M. P., 1998, Modern Catalytic Methodsfor Organic Synthesis with Diazo Compounds: From Cyclopropanes toYlides

← 1 2 3 4 5 →