Metal-catalyzed enantioselective allylation in asymmetric synthesis

被引:1264
作者
Lu, Zhan [2 ]
Ma, Shengming [1 ,2 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
[2] Zhejiang Univ, Dept Chem, Lab Mol Recognit & Synthesis, Hangzhou 310027, Peoples R China
关键词
allylation; asymmetric catalysis; chiral ligands; natural products; regioselectivity;
D O I
10.1002/anie.200605113
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Metal-catalyzed enantioselective allylation, which involves the substitution of allylic metal intermediates with a diverse range of different nucleophiles or SN2′-type allylic substitution, leads to the formation of C-H, -C, -O, -N, S, and other bonds with very high levels of asymmetric induction. The reaction may tolerate a broad range of functional groups and has been applied successfully to the synthesis of many natural products and new chiral compounds. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:258 / 297
页数:40
相关论文
共 447 条
[1]   Palladium-catalysed enantioselective synthesis of ibuprofen [J].
Acemoglu, L ;
Williams, JMJ .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2003, 196 (1-2) :3-11
[2]  
Adams E, 1999, J ORG CHEM, V64, P8256
[3]   Palladium-assisted routes to nucleosides [J].
Agrofoglio, LA ;
Gillaizeau, I ;
Saito, Y .
CHEMICAL REVIEWS, 2003, 103 (05) :1875-1916
[4]   Pd-Catalyzed asymmetric allylic alkylations using various diphenylphosphino(oxazolinyl)ferrocene ligands [J].
Ahn, KH ;
Cho, CW ;
Park, JW ;
Lee, SW .
TETRAHEDRON-ASYMMETRY, 1997, 8 (08) :1179-1185
[5]   New dihydroxy bis(oxazoline) ligands for the palladium-catalyzed asymmetric allylic alkylation:: Experimental investigations of the origin of the reversal of the enantioselectivity [J].
Aït-Haddou, H ;
Hoarau, O ;
Cramailére, D ;
Pezet, F ;
Daran, JC ;
Balavoine, GGA .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (03) :699-707
[6]   Novel chiral diamino-oligothiophenes as valuable ligands in Pd-catalyzed allylic alkylations. On the "primary" role of "secondary" interactions in asymmetric catalysis [J].
Albano, VG ;
Bandini, M ;
Melucci, M ;
Monari, M ;
Piccinelli, F ;
Tommasi, S ;
Umani-Ronchi, A .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1507-1512
[7]   Very efficient phosphoramidite ligand for asymmetric iridium-catalyzed allylic alkylation [J].
Alexakis, A ;
Polet, D .
ORGANIC LETTERS, 2004, 6 (20) :3529-3532
[8]   An effective enantioselective approach to the securinega alkaloids:: Total synthesis of (-)-norsecurinine [J].
Alibés, R ;
Bayón, P ;
de March, P ;
Figueredo, M ;
Font, J ;
García-García, E ;
González-Gálvez, D .
ORGANIC LETTERS, 2005, 7 (22) :5107-5109
[9]   Sulfur-imine mixed donor chelate ligands for asymmetric catalysis: enantioselective allylic alkylation [J].
Anderson, JC ;
James, DS ;
Mathias, JP .
TETRAHEDRON-ASYMMETRY, 1998, 9 (05) :753-756
[10]   Palladium catalysed Heck and enantioselective allylic substitution reactions using reverse phase silica supports [J].
Anson, MS ;
Mirza, AR ;
Tonks, L ;
Williams, JMJ .
TETRAHEDRON LETTERS, 1999, 40 (39) :7147-7150