Copper-catalyzed synthesis of enantioenriched tetraarylethanes

被引:18
作者
Jen, Wendy S. [1 ]
Truppo, Matthew D. [1 ]
Amos, Deborah [1 ]
Devine, Paul [1 ]
McNevin, Michael [1 ]
Biba, Mirlinda [1 ]
Campos, Kevin R. [1 ]
机构
[1] Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA
关键词
D O I
10.1021/ol7027543
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein we report the asymmetric synthesis of 1,2-dipyridyl-1,2-diarylethanes via an unusual Cu(I)-catalyzed dimerization reaction. Subjection of a variety of enantioenriched substituted 2-pyridyl alcohols to a one-pot protocol generates the desired products in good yields and diastereoselectivities and with ee's up to >99%.
引用
收藏
页码:741 / 744
页数:4
相关论文
共 30 条
[21]   Nickel-catalyzed cross-couplings of organosillicon reagents with unactivated secondary alkyl bromides [J].
Powell, DA ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (25) :7788-7789
[22]  
SCHLOGL K, 1982, SYNTHESIS-STUTTGART, P50
[23]  
SKATTEBOL L, 1970, ORGANOMET CHEM, V24, P547
[24]   Hiyama reactions of activated and unactivated secondary alkyl halides catalyzed by a nickel/norephedrine complex [J].
Strotman, Neil A. ;
Sommer, Stefan ;
Fu, Gregory C. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (19) :3556-3558
[25]   Enzyme-catalyzed enantioselective diaryl ketone reductions [J].
Truppo, Matthew D. ;
Pollard, David ;
Devine, Paul .
ORGANIC LETTERS, 2007, 9 (02) :335-338
[26]   Palladium-catalyzed reaction of 2-hydroxy-2-methylpropiophenone with aryl bromides: A unique multiple arylation via successive C-C and C-H bond cleavages [J].
Wakui, H ;
Kawasaki, S ;
Satoh, T ;
Miura, M ;
Nomura, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (28) :8658-8659
[27]   TRANSITION-METAL-CATALYZED SUBSTITUTION-REACTION OF ALLYLIC PHOSPHATES WITH GRIGNARD-REAGENTS [J].
YANAGISAWA, A ;
NOMURA, N ;
YAMAMOTO, H .
TETRAHEDRON, 1994, 50 (20) :6017-6028
[28]  
YANAGISAWA A, 1993, SYNLETT, P689
[29]  
YMADA Y, 1981, CHEM LETT, P1277
[30]   Cross-couplings of unactivated secondary alkyl halides: Room-temperature nickel-catalyzed Negishi reactions of alkyl bromides and iodides [J].
Zhou, JR ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (48) :14726-14727