Catalytic Stereospecific Substitution of Enantioenriched Allylic Alcohols with Sodium Sulfinates

被引：47
作者：
Ma, Xian-Tao [1 ]
Dai, Rui-Han [1 ]
Zhang, Juan [1 ]
Gu, Yonghong [1 ]
Tian, Shi-Kai [1 ]
机构：
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 14-15期
基金：
中国国家自然科学基金;
关键词：
alcohols; palladium; stereospecificity; substitution; sulfones; 1,3-CHIRALITY TRANSFER; ASYMMETRIC-SYNTHESIS; KINETIC RESOLUTION; BOND FORMATION; C-C; OXYPALLADATION; AMINES; STEREOCHEMISTRY; SULFONYLATION; INDUCTION;
D O I：
10.1002/adsc.201400187
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An unprecedented stereospecific substitution reaction of enantioenriched allylic alcohols with sodium sulfinates has been developed for the asymmetric synthesis of allylic sulfones with excellent ee. A range of highly enantioenriched allylic alcohols smoothly underwent palladium diacetate/racemic 2,2'-bis(diphenylphosphino)-1,1'-binaphthylcatalyzed substitution with sodium sulfinates to give structurally diverse a-chiral allylic sulfones in moderate to excellent yields with complete retention of configuration. This study paves the way for the direct stereospecific substitution of enantioenriched allylic alcohols with sulfur nucleophiles.
引用
收藏
页码：2984 / 2988
页数：5
相关论文
共 70 条
  • [1] [Anonymous], 2013, Angew. Chem
  • [2] [Anonymous], 2009, ANGEW CHEM-GER EDIT
  • [3] Catalytic Enantioselective Alkylations with Allylic Alcohols
    Bandini, Marco
    Cera, Gianpiero
    Chiarucci, Michel
    [J]. SYNTHESIS-STUTTGART, 2012, 44 (04): : 504 - 512
  • [4] Allylic Alcohols: Sustainable Sources for Catalytic Enantioselective Alkylation Reactions
    Bandini, Marco
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) : 994 - 995
  • [5] Carey F.A., 2007, ADV ORG CHEM
  • [6] Palladium-triethylborane-triggered direct and regioselective conversion of allylic alcohols to allyl phenyl sulfones
    Chandrasekhar, S
    Jagadeshwar, V
    Saritha, B
    Narsihmulu, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) : 6506 - 6507
  • [7] PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC SULFONYLATION
    EICHELMANN, H
    GAIS, HJ
    [J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (03) : 643 - 646
  • [8] Synthesis and antimicrobial evaluation of farnesyl diphosphate mimetics
    Fairlamb, IJS
    Dickinson, JM
    O'Connor, R
    Cohen, LH
    van Thiel, CF
    [J]. BIOORGANIC CHEMISTRY, 2003, 31 (01) : 80 - 97
  • [9] Highly selective palladium catalyzed kinetic resolution and enantioselective substitution of racemic allylic carbonates with sulfur nucleophiles: Asymmetric synthesis of allylic sulfides, allylic sulfones, and allylic alcohols
    Gais, HJ
    Jagusch, T
    Spalthoff, N
    Gerhards, F
    Frank, M
    Raabe, G
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (17) : 4202 - 4221
  • [10] Pd-catalyzed asymmetric synthesis of allylic tert-butyl sulfones and sulfides:: Kinetic resolution of the allylic substrate by a chiral Pd-complex
    Gais, HJ
    Eichelmann, H
    Spalthoff, N
    Gerhards, F
    Frank, M
    Raabe, G
    [J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (02) : 235 - 248
1234567