Asymmetric 1,4-Conjugate Addition of Diarylphosphines to α,β,γ,δ-Unsaturated Ketones Catalyzed by Transition-Metal Pincer Complexes

被引:49
作者
Yang, Xiang-Yuan [1 ]
Tay, Wee Shan [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
关键词
ENANTIOSELECTIVE 1,6-CONJUGATE ADDITION; HETEROCYCLIC CARBENE LIGANDS; RAY CRYSTAL-STRUCTURES; METHYL ISOCYANOACETATE; CONJUGATE ADDITION; STERIC PROPERTIES; ALDOL REACTION; AQUEOUS-MEDIA; BURIED VOLUME; PALLADIUM;
D O I
10.1021/acs.organomet.5b00787
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An enantioselective asymmetric 1,4-addition of diarylphosphines to linear alpha,beta,gamma,delta-unsaturated dienones was developed. A series of chiral PCP- and PCN-transition-metal (Pd, Pt and Ni) pincers, themselves prepared catalytically via asymmetric hydrophosphination, were sequentially screened to reveal the roles of backbone architecture and metal ion in catalyst design. The selected ester-functionalized PCP-palladium pincer afforded the chiral 1,4-phosphine adducts in excellent yields with up to >99% ee. The same catalyst when utilized for the hydrophosphination of an alpha,beta,gamma,delta-unsaturated malonate ester also revealed the critical role played by the ester functionality on the ligand backbone in dictating the enantioselectivity of the 1,6-adduct.
引用
收藏
页码:5196 / 5201
页数:6
相关论文
共 59 条
  • [1] Stereoselective Pincer-Complex Catalyzed C-H Functionalization of Benzyl Nitriles under Mild Conditions. An Efficient Route to β-Aminonitriles
    Aydin, Juhanes
    Conrad, Cathrin S.
    Szabo, Kalman J.
    [J]. ORGANIC LETTERS, 2008, 10 (22) : 5175 - 5178
  • [2] Synthesis and catalytic application of chiral 1,1′-bi-2-naphthol- and biphenanthrol-based pincer complexes:: Selective allylation of sulfonimines with allyl stannane and allyl trifluoroborate
    Aydin, Juhanes
    Kumar, K. Senthil
    Sayah, Mahmoud J.
    Wallner, Olov A.
    Szabo, Kalman J.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (13) : 4689 - 4697
  • [3] Synthesis and Resolution of Planar-Chiral Ruthenium-Palladium Complexes with ECE′ Pincer Ligands
    Bonnet, Sylvestre
    Li, Jie
    Siegler, Maxime A.
    von Chrzanowski, Lars S.
    Spek, Anthony L.
    van Koten, Gerard
    Gebbink, Robertus J. M. Klein
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (14) : 3340 - 3343
  • [4] Borner A., 2008, Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications
  • [5] REGIOSELECTIVE GAMMA-ELIMINATION OF SULFONES UNDER MICHAEL REACTION CONDITIONS
    BRITTENKELLY, MR
    WILLIS, BJ
    BARTON, DHR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (24) : 5027 - 5028
  • [6] Reduction of tertiary phosphine oxides with DIBAL-H
    Busacca, Carl A.
    Raju, Ravinder
    Grinberg, Nelu
    Haddad, Nizar
    James-Jones, Paul
    Lee, Heewon
    Lorenz, Jon C.
    Saha, Anjan
    Senanayake, Chris H.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (04) : 1524 - 1531
  • [7] Ambient Temperature Hydrophosphination of Internal, Unactivated Alkynes and Allenyl Phosphineoxides with Phosphine Borane Complexes
    Busacca, Carl A.
    Farber, Elisa
    DeYoung, Jay
    Campbell, Scot
    Gonnella, Nina C.
    Grinberg, Nelu
    Haddad, Nizar
    Lee, Heewon
    Ma, Shengli
    Reeves, Diana
    Shen, Sherry
    Senanayake, Chris H.
    [J]. ORGANIC LETTERS, 2009, 11 (24) : 5594 - 5597
  • [8] Enantioselective phospha-Michael addition of diarylphosphines to β,γ-unsaturated α-ketoesters and amides
    Chew, Renta Jonathan
    Teo, Kai Yuan
    Huang, Yinhua
    Li, Bin-Bin
    Li, Yongxin
    Pullarkat, Sumod A.
    Leung, Pak-Hing
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (63) : 8768 - 8770
  • [9] Enantioselective Addition of Diphenylphosphine to 3-Methyl-4-nitro-5-alkenylisoxazoles
    Chew, Renta Jonathan
    Huang, Yinhua
    Li, Yongxin
    Pullarkat, Sumod A.
    Leung, Pak-Hing
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (07) : 1403 - 1408
  • [10] Percent buried volume for phosphine and N-heterocyclic carbene ligands: steric properties in organometallic chemistry
    Clavier, Herve
    Nolan, Steven P.
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (06) : 841 - 861