Catalytic asymmetric deprotonation of phosphine boranes and sulfides as a route to P-stereogenic compounds

被引:34
作者
Gammon, Jonathan J. [1 ]
Canipa, Steven J. [1 ]
O'Brien, Peter [1 ]
Kelly, Brian [2 ]
Taylor, Sven [3 ]
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
[2] Nova Ctr, Celt Catalysts Ltd, Dublin 4, Ireland
[3] F Hoffmann La Roche & Co Ltd, CH-4070 Basel, Switzerland
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1039/b806864j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A comparison between phosphine boranes and sulfides in their catalytic asymmetric deprotonation using organolithiums and sub-stoichiometric amounts of (-)-sparteine has revealed superior catalytic efficiency in the phosphine sulfide deprotonation.
引用
收藏
页码:3750 / 3752
页数:3
相关论文
共 25 条
[1]   New P-chirogenic phosphine ligands and their use in catalytic asymmetric reactions [J].
Crépy, KVL ;
Imamoto, T .
NEW ASPECTS IN PHOSPHORUS CHEMISTRY III, 2003, 229 :1-40
[2]  
CREPY KVL, 2003, ADV SYNTH CATAL, V103, P3029
[3]   A readily-accessible (+)-sparteine surrogate [J].
Dearden, MJ ;
Firkin, CR ;
Hermet, JPR ;
O'Brien, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (40) :11870-11871
[4]   SYNTHESIS OF (+)-(1R,2S,9S)-11-METHYL-7,11-DIAZATRICYCLO[7.3.1.0(2,7)]TRIDECANE, A (+)-SPARTEINE SURROGATE [J].
Dixon, Amanda J. ;
McGrath, Matthew J. ;
O'Brien, Peter .
ORGANIC SYNTHESES, 2006, 83 :141-+
[5]   Catalytic asymmetric synthesis of ferrocenes and P-stereogenic bisphosphines [J].
Genet, Cedric ;
Canipa, Steven J. ;
O'Brien, Peter ;
Taylor, Sven .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (29) :9336-9337
[6]   Preparation of optically pure P-stereogenic trivalent phosphorus compounds [J].
Grabulosa, Arnald ;
Granell, Jaume ;
Muller, Guillermo .
COORDINATION CHEMISTRY REVIEWS, 2007, 251 (1-2) :25-90
[7]   Asymmetric hydrogenation catalyzed by a rhodium complex of (R)-(tert-butylmethylphosphino)(di-tert-butylphosphino)methane:: Scope of enantioselectivity and mechanistic study [J].
Gridnev, Ilya D. ;
Imamoto, Tsuneo ;
Hoge, Garrett ;
Kouchi, Mitsuhiro ;
Takahashi, Hidetoshi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (08) :2560-2572
[8]   Highly selective asymmetric hydrogenation using a three hindered quadrant bisphosphine rhodium catalyst [J].
Hoge, G ;
Wu, HP ;
Kissel, WS ;
Pflum, DA ;
Greene, DJ ;
Bao, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (19) :5966-5967
[9]   An air-stable P-chiral phosphine ligand for highly enantioselective transition-metal-catalyzed reactions [J].
Imamoto, T ;
Sugita, K ;
Yoshida, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (34) :11934-11935
[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