Palladium-Catalyzed Asymmetric 1,6-Addition of Diarylphosphines to Allylidenemalonates for Chiral Phosphine Synthesis

被引:11
作者
Wei, Xu [1 ]
Lu, Junzhu [2 ]
Duan, Wei-Liang [3 ]
机构
[1] Shanghai Inst Technol, Sch Chem & Environm Engn, Shanghai 201418, Peoples R China
[2] East China Univ Sci & Technol, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源
SYNTHESIS-STUTTGART | 2016年 / 48卷 / 23期
基金
美国国家科学基金会;
关键词
asymmetric 1,6-addition; pincer palladium catalyst; chiral phosphines; allylidenemalonates; BAYLIS-HILLMAN CARBONATES; PCN PINCER PALLADIUM(II); P-STEREOGENIC PHOSPHINES; ENANTIOSELECTIVE SYNTHESIS; 1,6-CONJUGATE ADDITION; SECONDARY PHOSPHINES; ACTIVATED OLEFINS; ARYLBORONIC ACIDS; MICHAEL REACTION; SULFONIC ESTERS;
D O I
10.1055/s-0035-1562456
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A pincer-palladium-catalyzed asymmetric 1,6-addition of diarylphosphines to allylidenemalonates has been developed for the synthesis of chiral allylic phosphines with up to 89% ee under mild conditions.
引用
收藏
页码:4155 / 4160
页数:6
相关论文
共 100 条
[1]  
Albrecht M, 2001, ANGEW CHEM INT EDIT, V40, P3750, DOI 10.1002/1521-3773(20011015)40:20<3750::AID-ANIE3750>3.0.CO
[2]  
2-6
[3]  
Bansal RK, 2010, TOP HETEROCYCL CHEM, V21, P1, DOI 10.1007/978-3-642-12254-5
[4]   Organocatalytic asymmetric hydrophosphination of nitroalkenes [J].
Bartoli, Giuseppe ;
Bosco, Marcella ;
Carlone, Armando ;
Locatelli, Manuela ;
Mazzanti, Andrea ;
Sambri, Letizia ;
Melchiorre, Paolo .
CHEMICAL COMMUNICATIONS, 2007, (07) :722-724
[5]   Organocatalytic asymmetric 1,6-additions of β-ketoesters and glycine imine [J].
Bernardi, Luca ;
Lopez-Cantarero, Jesus ;
Niess, Barbara ;
Jlrgensen, Karl Anker .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (17) :5772-5778
[6]   Organocatalytic Asymmetric 1,6-Addition Reactions [J].
Biju, Akkattu T. .
CHEMCATCHEM, 2011, 3 (12) :1847-1849
[7]   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
[8]  
Borner A., 2008, PHOSPHORUS LIGANDS A, V1-3
[9]   Palladium-catalyzed enantioselective allylic phosphination [J].
Butti, Pietro ;
Rochat, Raphael ;
Sadow, Aaron D. ;
Togni, Antonio .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (26) :4878-4881
[10]   Organocatalytic asymmetric hydrophosphination of α,β-Unsaturated aldehydes [J].
Carlone, Armando ;
Bartoli, Giuseppe ;
Bosco, Marcella ;
Sambri, Letizia ;
Melchiorre, Paolo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (24) :4504-4506