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

被引：114
作者：
Albinati, A
Pregosin, PS
Wick, K
机构：
[1] Lab. für Anorganische Chemie, ETH Zentrum
来源：
ORGANOMETALLICS | 1996年 / 15卷 / 10期
关键词：
D O I：
10.1021/om950983m
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The new ferrocene-based P,S-chiral auxiliary 1, derived from thioglucose, has been prepared and used in the palladium-catalyzed enantioselective allylic alkylation reaction. The X-ray structure of the allyl cationic complex [Pd(eta(3)-PhCHCHCHPh)(1)]CF3SO3 (2) reveals a markedly rotated 1,3-diphenylallyl ligand such that the terminal allyl carbon C(3), trans to the phosphorus donor, is ca. 0.85(3) Angstrom below the coordination plane. This distortion is pertinent to the Pd(0) transition state complex expected in the allylic alkylation reaction.
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收藏
页码：2419 / 2421
页数：3
相关论文
共 31 条
[1]   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
[2]  
[Anonymous], HELV CHIM ACTA
[3]   1,3-DIPHENYLALLYL COMPLEXES OF PALLADIUM(II) - NMR, X-RAY, AND CATALYTIC STUDIES [J].
BARBARO, P ;
PREGOSIN, PS ;
SALZMANN, R ;
ALBINATI, A ;
KUNZ, RW .
ORGANOMETALLICS, 1995, 14 (11) :5160-5170
[4]   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
[5]   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
[6]   SYNTHESIS AND STRUCTURE OF PYRAZOLE-CONTAINING FERROCENYL LIGANDS FOR ASYMMETRIC CATALYSIS [J].
BURCKHARDT, U ;
HINTERMANN, L ;
SCHNYDER, A ;
TOGNI, A .
ORGANOMETALLICS, 1995, 14 (11) :5415-5425
[7]   C-2 DIAMINE, PSEUDO-C-2 POLY(AMIDE) AND POLY(UREA) AS CHIRAL INDUCTORS IN ASYMMETRIC CATALYSIS [J].
GAMEZ, P ;
DUNJIC, B ;
FACHE, F ;
LEMAIRE, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (12) :1417-1418
[8]   PALLADIUM PI-ALLYL CHEMISTRY OF NEW P,S BIDENTATE LIGANDS - SELECTIVE BUT VARIABLE DYNAMICS IN THE ISOMERIZATION OF THE ETA(3)-C3H5 AND ETA(3)-PHCHCHCHPH PI-ALLYL LIGANDS [J].
HERRMANN, J ;
PREGOSIN, PS ;
SALZMANN, R ;
ALBINATI, A .
ORGANOMETALLICS, 1995, 14 (07) :3311-3318
[9]   ASYMMETRIC INDUCTION REACTIONS .7. PALLADIUM-CATALYZED ASYMMETRIC SULFONYLATIONS OF ALPHA,GAMMA-DISUBSTITUTED ALLYLIC ACETATES WITH CHIRAL PHOSPHINE-LIGANDS [J].
HIRASAWA, K ;
KAWAMATA, M ;
HIROI, K .
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1994, 114 (02) :111-118
[10]   NEW CHIRAL BETA-PHOSPHINOCARBOXYLIC ACIDS AND THEIR APPLICATION IN PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC ALKYLATIONS [J].
KNUHL, G ;
SENNHENN, P ;
HELMCHEN, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (18) :1845-1846
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