Highly Regio- and Diastereoselective Anionic [3+2] Cycloaddition under Phase Transfer Catalytic Conditions

被引:23
作者
Gembus, Vincent
Postikova, Svetlana
Levacher, Vincent
Briere, Jean-Francois [1 ]
机构
[1] Univ Rouen, CNRS, UMR, COBRA, F-76821 Mont St Aignan, France
关键词
CYCLIZATION-ELIMINATION ROUTE; CYCLOPENTENYL SULFONES; CONSTRUCTION; UNITS;
D O I
10.1021/jo2005268
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly trans and regioselective anionic formal [3 + 2] cycloaddition was achieved with allylic sulfones having an MBH acrylamide backbone under phase transfer organocatalytic conditions giving rise to the formation of unprecedented densely substituted cyclopentene derivatives.
引用
收藏
页码:4194 / 4199
页数:6
相关论文
共 31 条
[1]   Sulfones: new reagents in organocatalysis [J].
Alba, Andrea-Nekane R. ;
Companyo, Xavier ;
Rios, Ramon .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (06) :2018-2033
[2]   Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry [J].
Basavaiah, Deevi ;
Reddy, Bhavanam Sekhara ;
Badsara, Satpal Singh .
CHEMICAL REVIEWS, 2010, 110 (09) :5447-5674
[3]   AN ANIONIC 3 + 2 CYCLIZATION ELIMINATION ROUTE TO CYCLOPENTENES [J].
BEAK, P ;
BURG, DA .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1647-1654
[4]   AN ANIONIC 3+2 CYCLIZATION-ELIMINATION ROUTE TO CYCLOPENTENES [J].
BEAK, P ;
BURG, DA .
TETRAHEDRON LETTERS, 1986, 27 (49) :5911-5914
[5]   LiOH•H2O as a novel dual activation catalyst for highly efficient and easy synthesis of 1,3-diaryl-2-propenones by Claisen-Schmidt condensation under mild conditions [J].
Bhagat, S ;
Sharma, R ;
Sawant, DM ;
Sharma, L ;
Chakraborti, AK .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 244 (1-2) :20-24
[6]   Enantioselective catalysis and complexity generation from allenoates [J].
Cowen, Bryan J. ;
Miller, Scott J. .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3102-3116
[7]   Recent developments in the synthesis of prostaglandins and analogues [J].
Das, Saibal ;
Chandrasekhar, Srivari ;
Yadav, Jhillu Singh ;
Gree, René .
CHEMICAL REVIEWS, 2007, 107 (07) :3286-3337
[8]   A stereodivergent synthesis of β-hydroxy-α-methylene lactones via vinyl epoxides [J].
Davoust, Marion ;
Cantagrel, Frederic ;
Metzner, Patrick ;
Briere, Jean-Francois .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (11) :1981-1993
[9]   Evolving Organic Synthesis Fostered by the Pluripotent Phenylsulfone Moiety [J].
El-Awa, Ahmad ;
Noshi, Mohammad N. ;
du Jourdin, Xavier Mollat ;
Fuchs, Philip L. .
CHEMICAL REVIEWS, 2009, 109 (06) :2315-2349
[10]   Enantioselective [3+2] Cycloaddition of Allenes to Acrylates Catalyzed by Dipeptide-Derived Phosphines: Facile Creation of Functionalized Cyclopentenes Containing Quaternary Stereogenic Centers [J].
Han, Xiaoyu ;
Wang, Youqing ;
Zhong, Fangrui ;
Lu, Yixin .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (06) :1726-1729