Synthesis of Arylethyl (E)-Styrylsulfones and Arylsulfones by One-Pot DIBAL-H/NaH-Mediated Reaction of β-Ketosulfones

被引:18
作者
Chang, Meng-Yang [1 ]
Chen, Yi-Chia [1 ]
Chan, Chieh-Kai [1 ]
机构
[1] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 807, Taiwan
关键词
aldol reaction; aluminum; condensation; sulfones; tandem reaction; UNSYMMETRICAL DIARYL SULFONES; KETO-SULFONES; ACID SALTS; ARYL; FACILE; SULFONYLATION; SULFOXIDES; VERSATILE; CATALYST; HALIDES;
D O I
10.1055/s-0033-1339117
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile one-pot synthetic route for preparing a series of arylethyl (E)-styrylsulfones or arylethyl arylsulfones is developed. The efficient one-pot DIBAL-H/NaH-mediated route includes reduction of -benzyl--arylketosulfones and retroaldol/aldol or retroaldol reaction of the resulting intermediate. The DIBAL-H/NaH-mediated reaction mechanism has been discussed.
引用
收藏
页码:1739 / 1744
页数:6
相关论文
共 62 条
[1]   A Regio- and Diastereoselective Platinum-Catalyzed Tandem [2+1]/[3+2] Cycloaddition Sequence [J].
Achard, Thierry ;
Lepronier, Aymeric ;
Gimbert, Yves ;
Clavier, Herve ;
Giordano, Laurent ;
Tenaglia, Alphonse ;
Buono, Gerard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (15) :3552-3556
[2]   PHORBOL ESTERS STIMULATE THE PHOSPHORYLATION OF C-JUN BUT NOT V-JUN - REGULATION BY THE N-TERMINAL DELTA DOMAIN [J].
ADLER, V ;
FRANKLIN, CC ;
KRAFT, AS .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1992, 89 (12) :5341-5345
[3]   Second-Generation Process Research Towards Eletriptan: A Fischer Indole Approach [J].
Ashcroft, Christopher P. ;
Hellier, Paul ;
Pettman, Alan ;
Watkinson, Simon .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2011, 15 (01) :98-103
[4]   Unsymmetrical diaryl Sulfones through palladium-catalyzed coupling of aryl boronic acids and arylsulfonyl chlorides [J].
Bandgar, BP ;
Bettigeri, SV ;
Phopase, J .
ORGANIC LETTERS, 2004, 6 (13) :2105-2108
[5]   An efficient copper catalyst for the formation of sulfones from sulfinic acid salts and aryl iodides [J].
Baskin, JM ;
Wang, ZY .
ORGANIC LETTERS, 2002, 4 (25) :4423-4425
[6]   Potassium hydroxide-mediated novel rearrangement of 2-alkyl-sulfonyl-2-arylsulfonyl-1-phenylethanones to 1-aryl-2-(arylsulfonylmethanesulfonyl)ethanones [J].
Bin, JK ;
Lee, JS ;
Kim, K .
ORGANIC LETTERS, 2004, 6 (23) :4297-4300
[7]   Unsymmetrical diaryl sulfones and aryl vinyl sulfones through palladium-catalyzed coupling of aryl and vinyl halides or triflates with sulfinic acid salts [J].
Cacchi, S ;
Fabrizi, G ;
Goggiamani, A ;
Parisi, LM ;
Bernini, R .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5608-5614
[8]   An efficient palladium-catalyzed synthesis of unsymmetrical diaryl sulfones from aryl bromides/triflates and arenesulfinates [J].
Cacchi, S ;
Fabrizi, G ;
Goggiamani, A ;
Parisi, LM .
SYNLETT, 2003, (03) :361-364
[9]   Unsymmetrical diaryl sulfones through palladium-catalyzed coupling of aryl iodides and arenesulfinates [J].
Cacchi, S ;
Fabrizi, G ;
Goggiamani, A ;
Parisi, LM .
ORGANIC LETTERS, 2002, 4 (26) :4719-4721
[10]   Rapid synthesis of sulfone derivatives as potential anti-infectious agents [J].
Curti, C. ;
Laget, M. ;
Carle, A. Ortiz ;
Gellis, A. ;
Vanelle, P. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2007, 42 (06) :880-884