1-Phosphino-2-sulfenylferrocenes:: efficient ligands in enantioselective palladium-catalyzed allylic substitutions and ring opening of 7-oxabenzonorbornadienes

被引:69
作者
Priego, J [1 ]
Mancheño, OG [1 ]
Cabrera, S [1 ]
Arrayás, RG [1 ]
Llamas, T [1 ]
Carretero, JC [1 ]
机构
[1] Univ Autonoma Madrid, Dept Quim Organ, Fac Ciencias, E-28049 Madrid, Spain
关键词
D O I
10.1039/b207344g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The readily available 1-phosphino-2-sulfenylferrocenes 1 provide very high enantioselectivities in Pd-catalyzed allylic substitution reactions and alkylative ring opening of 7-oxabenzonorbornadiene with dialkylzinc reagents.
引用
收藏
页码:2512 / 2513
页数:2
相关论文
共 20 条
[1]   A new P,S-Chiral auxiliary derived from thioglucose. X-ray structure of a palladium 1,3-diphenylallyl complex with a strongly rotated allyl ligand [J].
Albinati, A ;
Pregosin, PS ;
Wick, K .
ORGANOMETALLICS, 1996, 15 (10) :2419-2421
[2]   Catalytic asymmetric oxidation of tert-butyl disulfide.: Synthesis of tert-butanesulfinamides, tert-butyl sulfoxides, and tert-butanesulfinimines [J].
Cogan, DA ;
Liu, GC ;
Kim, KJ ;
Backes, BJ ;
Ellman, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (32) :8011-8019
[3]   HIGHLY ENANTIOSELECTIVE OXIDATION OF FERROCENYL SULFIDES [J].
DITER, P ;
SAMUEL, O ;
TAUDIEN, S ;
KAGAN, HB .
TETRAHEDRON-ASYMMETRY, 1994, 5 (04) :549-552
[4]  
Enders D, 2000, EUR J ORG CHEM, V2000, P3399
[5]   Application of chiral mixed phosphorus/sulfur ligands to palladium-catalyzed allylic substitutions [J].
Evans, DA ;
Campos, KR ;
Tedrow, JS ;
Michael, FE ;
Gagné, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (33) :7905-7920
[6]  
Fagnou K, 2002, ANGEW CHEM INT EDIT, V41, P26, DOI 10.1002/1521-3773(20020104)41:1<26::AID-ANIE26>3.0.CO
[7]  
2-9
[8]   New chiral sulfoxide ligands possessing a phosphano or phosphanoamino functionality in palladium-catalyzed asymmetric allylic nucleophilic substitution reactions [J].
Hiroi, K ;
Suzuki, Y ;
Abe, I ;
Kawagishi, R .
TETRAHEDRON, 2000, 56 (27) :4701-4710
[9]   Chiral sulfur-containing 1,2-disubstituted ferrocenes [J].
Lagneau, NM ;
Chen, Y ;
Robben, PM ;
Sin, HS ;
Takasu, K ;
Chen, JS ;
Robinson, PD ;
Hua, DH .
TETRAHEDRON, 1998, 54 (26) :7301-7334
[10]   Mechanistic studies of the palladium-catalyzed ring opening of oxabicyclic alkenes with dialkylzinc [J].
Lautens, M ;
Hiebert, S ;
Renaud, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) :6834-6839