Pd-Catalyzed asymmetric allylic alkylations using various diphenylphosphino(oxazolinyl)ferrocene ligands

被引:102
作者
Ahn, KH [1 ]
Cho, CW [1 ]
Park, JW [1 ]
Lee, SW [1 ]
机构
[1] POHANG UNIV SCI & TECHNOL POSTECH,CTR BIOFUNCT MOL,POHANG 790784,SOUTH KOREA
关键词
CHIRAL BISPHOSPHINE LIGANDS; BIDENTATE NITROGEN LIGANDS; ENANTIOSELECTIVE CATALYSIS; PALLADIUM COMPLEXES; METAL-COMPLEXES; SUBSTITUTION; MECHANISM; INDUCTION; PHOSPHINOARYLOXAZOLINES; ALLYLATION;
D O I
10.1016/S0957-4166(97)00104-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Pd-Catalyzed asymmetric allylic alkylations have been studied using a series of chiral diphenylphosphino(oxazolinyl)ferrocene ligands 4-8. With these ligands, up to 99% and 63% ee are obtained for rac-(E)-1,3-diphenylprop-2-enyl-1-acetate and rac-(E)-1,3-dimethylprop-2-enyl-1-acetate, respectively, with dimethyl malonate as the nucleophile. Some of the ligands 4-6 generate corresponding Pd-catalysts more reactive than those formed from other known ligands. A noticeable influence of the planar chirality on the enantioselectivity is observed. Different coordination modes can be suggested for the distinguishable enantioselectivity and reactivity patterns observed in the reactions with the ligands 4-8. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:1179 / 1185
页数:7
相关论文
共 68 条
[1]   An efficient diastereoselective synthesis of chiral oxazolinylferrocene compounds [J].
Ahn, KH ;
Cho, CW ;
Baek, HH ;
Park, J ;
Lee, S .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) :4937-4943
[2]   STUDIES OF ALLYLIC SUBSTITUTION CATALYZED BY A PALLADIUM COMPLEX OF A C-2-SYMMETRICAL BIS(AZIRIDINE) - PREPARATION AND NMR SPECTROSCOPIC INVESTIGATION OF A CHIRAL PI-ALLYL SPECIES [J].
ANDERSSON, PG ;
HARDEN, A ;
TANNER, D ;
NORRBY, PO .
CHEMISTRY-A EUROPEAN JOURNAL, 1995, 1 (01) :12-16
[3]   TRANS-INFLUENCE - ITS MEASUREMENT AND SIGNIFICANCE [J].
APPLETON, TG ;
CLARK, HC ;
MANZER, LE .
COORDINATION CHEMISTRY REVIEWS, 1973, 10 (3-4) :335-422
[4]   ASYMMETRIC-SYNTHESIS - ASYMMETRIC CATALYTIC ALLYLATION USING PALLADIUM CHIRAL PHOSPHINE COMPLEXES [J].
AUBURN, PR ;
MACKENZIE, PB ;
BOSNICH, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) :2033-2046
[5]   Synthesis and applications of a new class of C2 symmetric phosphorus donor ligand for asymmetric catalysis. [J].
Brenchley, G ;
Fedouloff, M ;
Merifield, E ;
Wills, M .
TETRAHEDRON-ASYMMETRY, 1996, 7 (10) :2809-2812
[6]   AN UNUSUAL, SELECTIVE ETA(3)-ETA(1) ALLYL ISOMERIZATION IN A CHIRAL ALLYLIC ALKYLATION CATALYST [J].
BREUTEL, C ;
PREGOSIN, PS ;
SALZMANN, R ;
TOGNI, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (09) :4067-4068
[7]   MECHANISTIC AND SYNTHETIC STUDIES IN CATALYTIC ALLYLIC ALKYLATION WITH PALLADIUM COMPLEXES OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE [J].
BROWN, JM ;
HULMES, DI ;
GUIRY, PJ .
TETRAHEDRON, 1994, 50 (15) :4493-4506
[8]   Crystallographic and NMR studies on chiral palladium(II) allyl ferrocene-based P,N complexes [J].
Burckhardt, U ;
Gramlich, V ;
Hofmann, P ;
Nesper, R ;
Pregosin, PS ;
Salzmann, R ;
Togni, A .
ORGANOMETALLICS, 1996, 15 (16) :3496-3503
[9]   Enantioselective palladium catalyzed allylic substitution with sulfur-containing pyridine ligands [J].
Chelucci, G ;
Cabras, MA .
TETRAHEDRON-ASYMMETRY, 1996, 7 (04) :965-966
[10]   SULFIDES TETHERED TO OXAZOLINES - LIGANDS FOR ENANTIOSELECTIVE CATALYSIS [J].
DAWSON, GJ ;
FROST, CG ;
MARTIN, CJ ;
WILLIAMS, JMJ .
TETRAHEDRON LETTERS, 1993, 34 (48) :7793-7796