Asymmetric Synthesis of P-Stereogenic Phosphinic Amides via Pd(0)-Catalyzed Enantioselective Intramolecular C-H Arylation

被引:112
作者
Liu, Lantao [1 ]
Zhang, An-An
Wang, Yanfang [2 ]
Zhang, Fuqiang [1 ]
Zuo, Zhenzhen [1 ]
Zhao, Wen-Xian [1 ]
Feng, Cui-Lan [1 ]
Ma, Wenjin [2 ]
机构
[1] Shangqiu Normal Univ, Coll Chem & Chem Engn, Shangqiu 476000, Henan, Peoples R China
[2] Shanxi Normal Univ, Sch Chem & Mat Sci, Linfen 041004, Peoples R China
基金
中国国家自然科学基金;
关键词
CHIRAL PHOSPHORUS LIGANDS; COUPLING REACTIONS; INDOLINES; MECHANISM; OXIDES; DEPROTONATION; FERROCENES; ACCESS; SCOPE; HYDROPHOSPHINATION;
D O I
10.1021/acs.orglett.5b00122
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium-catalyzed enantioselective intramolecular C-H arylation of N-(2-haloaryl)-P,P-diphenylphosphinic amides furnishes P-stereogenic phosphine oxide derivatives in 61-99% yield with 88-97% ee. The catalyst generated in situ from a TADDOL-derived phosphoramide ligand and Pd(dba)(2) is optimum in terms of yield and enantioselectivities.
引用
收藏
页码:2046 / 2049
页数:4
相关论文
共 75 条
[1]   Enantioselective Palladium-Catalyzed Direct Arylations at Ambient Temperature: Access to Indanes with Quaternary Stereocenters [J].
Albicker, Martin R. ;
Cramer, Nicolai .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) :9139-9142
[2]   Enantioselective synthesis of 2-methyl indolines by palladium catalysed asymmetric C(sp3)-H activation/cyclisation [J].
Anas, Saithalavi ;
Cordi, Alex ;
Kagan, Henri B. .
CHEMICAL COMMUNICATIONS, 2011, 47 (41) :11483-11485
[3]   Highly enantiomerically enriched chlorophosphine boranes:: Synthesis and applications as P-chirogenic electrophilic blocks [J].
Bauduin, C ;
Moulin, D ;
Kaloun, EB ;
Darcel, C ;
Jugé, S .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4293-4301
[4]   General Strategy for the Synthesis of P-Stereogenic Compounds [J].
Berger, Olivier ;
Montchamp, Jean-Luc .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (43) :11377-11380
[5]   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
[6]  
Borner A., 2008, Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications
[7]   Water soluble phosphines - Part XV. Syntheses of multiply functionalized and chiral phosphine ligands by Pd-catalyzed P-C and C-C coupling reactions [J].
Brauer, DJ ;
Hingst, M ;
Kottsieper, KW ;
Liek, C ;
Nickel, T ;
Tepper, M ;
Stelzer, O ;
Sheldrick, WS .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 645 (1-2) :14-26
[8]   Enantioselective synthesis of P-stereogenic benzophospholanes via palladium-catalyzed intramolecular cyclization [J].
Brunker, Tim J. ;
Anderson, Brian J. ;
Blank, Natalia F. ;
Glueck, David S. ;
Rheingold, Arnold L. .
ORGANIC LETTERS, 2007, 9 (06) :1109-1112
[9]   Pd-catalyzed dynamic kinetic enantioselective arylation of silylphosphines [J].
Chan, Vincent S. ;
Bergman, Robert G. ;
Toste, F. Dean .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (49) :15122-+
[10]   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