P-chirogenic binaphthyl-substituted monophosphines:: Synthesis and use in enolate vinylation/arylation reactions

被引:76
作者
Hamada, T [1 ]
Buchwald, SL [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ol025563p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] New phosphine ligands possessing both axial chirality and a chirogenic phosphorus center were prepared from (R)-2-bromo-2'-N,N- (dimethylamino)-1,1'-binaphthyl (1) via a simple Li-halogen exchange protocol. The asymmetric vinylation of a ketone enolate with (RRp)-2-(tert-butylphenylphosphino)-2'- N,N-(dimethylamino)-1,1'-binaphthyl (2a) afforded the coupling product with good enantiomeric excess.
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页码:999 / 1001
页数:3
相关论文
共 29 条
[1]   PREPARATION AND USE OF C2-SYMMETRICAL BIS(PHOSPHOLANES) - PRODUCTION OF ALPHA-AMINO-ACID DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].
BURK, MJ ;
FEASTER, JE ;
NUGENT, WA ;
HARLOW, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10125-10138
[2]   Catalytic asymmetric vinylation of ketone enolates [J].
Chieffi, A ;
Kamikawa, K ;
Åhman, J ;
Fox, JM ;
Buchwald, SL .
ORGANIC LETTERS, 2001, 3 (12) :1897-1900
[3]   TITANIUM (IV) CATALYSIS IN THE REDUCTION OF PHOSPHINE OXIDES [J].
COUMBE, T ;
LAWRENCE, NJ ;
MUHAMMAD, F .
TETRAHEDRON LETTERS, 1994, 35 (04) :625-628
[4]   An improved catalyst for the asymmetric arylation of ketone enolates [J].
Hamada, T ;
Chieffi, A ;
Åhman, J ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) :1261-1268
[5]   Asymmetric hydrosilylation of styrenes catalyzed by palladium-MOP complexes: Ligand modification and mechanistic studies [J].
Hayashi, T ;
Hirate, S ;
Kitayama, K ;
Tsuji, H ;
Torii, A ;
Uozumi, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1441-1449
[6]   Rhodium-catalyzed asymmetric arylation of imines with organostannanes. Asymmetric synthesis of diarylmethylamines [J].
Hayashi, T ;
Ishigedani, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (05) :976-977
[7]   Chiral monodentate phosphine ligand MOP for transition metal-catalyzed asymmetric reactions [J].
Hayashi, T .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :354-362
[8]  
HAYASHI T, 1997, CHEM COMMUN, P3561
[9]   Phosphinooxazolines - A new class of versatile, modular P,N-ligands for asymmetric catalysis [J].
Helmchen, G ;
Pfaltz, A .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :336-345
[10]   P-chiral bis(trialkylphosphine) ligands and their use in highly enantioselective hydrogenation reactions [J].
Imamoto, T ;
Watanabe, J ;
Wada, Y ;
Masuda, H ;
Yamada, H ;
Tsuruta, H ;
Matsukawa, S ;
Yamaguchi, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (07) :1635-1636