Stereospecific Suzuki-Miyaura Coupling of Chiral α-(Acylamino)benzylboronic Esters with Inversion of Configuration

被引:220
作者
Ohmura, Toshimichi [1 ]
Awano, Tomotsugu [1 ]
Suginome, Michinori [1 ]
机构
[1] Kyoto Univ, Dept Synthet Chem & Biol Chem, Grad Sch Engn, Kyoto 6158510, Japan
关键词
C-N; ARYL; PALLADIUM; HALIDES; ACID; ALKYLBORANES; DERIVATIVES; RETENTION; TRANSMETALATION; STEREOCHEMISTRY;
D O I
10.1021/ja106632j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first invertive B-alkyl Suzuki-Miyaura coupling has been achieved. The coupling of enantioenriched alpha-(acylamino)benzylboronic esters with aryl bromides and chlorides took place efficiently in toluene at 80 degrees C in the presence of Pd(dba)(2) (5 mol %), XPhos (10 mol %), K(2)CO(3) (3 equiv), and H(2)O (2 equiv). The reaction proceeded with inversion of configuration to give diarylmethanamine derivatives in high yields with high conservation of enantiomeric excesses.
引用
收藏
页码:13191 / 13193
页数:3
相关论文
共 38 条
[1]  
BERGBREITER DE, 1976, J ORGANOMET CHEM, V121, P19
[2]   DERIVATIVES OF TETRAHEDRAL BORONIC ACIDS [J].
BIEDRZYCKI, M ;
SCOUTEN, WH ;
BIEDRZYCKA, Z .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 431 (03) :255-270
[3]   (S)-(+)-N-acetylphenylglycineboronic acid:: A chiral derivatizing agent for Ee determination of 1,2-diols [J].
Caselli, E ;
Danieli, C ;
Morandi, S ;
Bonfiglio, B ;
Forni, A ;
Prati, F .
ORGANIC LETTERS, 2003, 5 (25) :4863-4866
[4]   Diastereoselective synthesis of 1,2,3-substituted potassium cyclopropyl trifluoroborates via an unusual zinc-boron exchange [J].
Charette, AB ;
Mathieu, S ;
Fournier, JF .
SYNLETT, 2005, (11) :1779-1782
[5]   Synthesis of contiguous cyclopropanes by palladium-catalyzed Suzuki-type cross-coupling reactions. [J].
Charette, AB ;
DeFreitasGil, RP .
TETRAHEDRON LETTERS, 1997, 38 (16) :2809-2812
[6]  
Chemler SR, 2001, ANGEW CHEM INT EDIT, V40, P4544, DOI 10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO
[7]  
2-N
[8]   Expanding the scope of transformations of organoboron species: carbon-carbon bond formation with retention of configuration [J].
Crudden, Cathleen M. ;
Glasspoole, Ben W. ;
Lata, Christopher J. .
CHEMICAL COMMUNICATIONS, 2009, (44) :6704-6716
[9]   On the Absolute Configurational Stability of Bromonium and Chloronium Ions [J].
Denmark, Scott E. ;
Burk, Matthew T. ;
Hoover, Andrew J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) :1232-+
[10]   Synthesis and Reactivity of Enantiomerically Enriched Thiiranium Ions [J].
Denmark, Scott E. ;
Vogler, Thomas .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (43) :11737-11745