Molecular structure of 1,3-disubstituted pi-allyl palladium(II) complexes with a chiral diphosphine: The intermediate of palladium-catalyzed asymmetric allylic alkylation

被引：20

作者：

Yamaguchi, M ^{[1
]}

Yabuki, M ^{[1
]}

Yamagishi, T ^{[1
]}

Sakai, K ^{[1
]}

Tsubomura, T ^{[1
]}

机构：

[1] SEIKEI UNIV, FAC ENGN, DEPT IND CHEM, MUSASHINO, TOKYO 180, JAPAN

来源：

CHEMISTRY LETTERS | 1996年 / 03期

关键词：

D O I：

10.1246/cl.1996.241

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Structural studies by X-ray analysis and NMR spectroscopy of the pi-allyl complex, [Pd(eta(3)-1,3-diphenylallyl)((S)-BINAP)]-PF6 . AcOEt, have been carried out, and revealed the stereochemical feature for the intermediate of palladium-catalyzed asymmetric allylic alkylation. The dissimilarity of the two phenyl groups attached to the pi-allyl moiety is assumed to be one of the origin of the selectivity. In solution two configurational isomers, (syn, syn) and (syn, anti), exist.

引用

页码：241 / 242

页数：2

共 15 条

[1] SUCCESSFUL APPLICATION OF A FORGOTTEN PHOSPHINE IN ASYMMETRIC CATALYSIS - A 9-PHOSPHABICYCLO[3.3.1]NON-9-YL FERROCENE DERIVATIVE AS CHIRAL LIGAND [J].

ABBENHUIS, HCL ;

BURCKHARDT, U ;

GRAMLICH, V ;

KOLLNER, C ;

PREGOSIN, PS ;

SALZMANN, R ;

TOGNI, A .

ORGANOMETALLICS, 1995, 14 (02) :759-766

[2] 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

[3] NUCLEAR-MAGNETIC-RESONANCE AND CRYSTALLOGRAPHIC STUDIES OF CHIRAL ETA-3-ALLYL PALLADIUM(II) COMPLEXES AND ASYMMETRIC ALLYLIC ALKYLATION OF PROPEN-2-YL ACETATES [J].

CESAROTTI, E ;

GRASSI, M ;

PRATI, L ;

DEMARTIN, F .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1991, (08) :2073-2080

[4] STRUCTURE OF [PD(ETA-3-C(XYL)2CHCHPH)(S,S-PPH2(CHME)2PPH2)]BPH4 - A CATALYST FOR ASYMMETRIC ALLYLIC ALKYLATION REACTIONS [J].

FARRAR, DH ;

PAYNE, NC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) :2054-2058

[5] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE METAL-COMPLEXES [J].

HAYASHI, T .

PURE AND APPLIED CHEMISTRY, 1988, 60 (01) :7-12

[6] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE TRANSITION-METAL COMPLEXES .8. PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC AMINATION [J].

HAYASHI, T ;

YAMAMOTO, A ;

ITO, Y ;

NISHIOKA, E ;

MIURA, H ;

YANAGI, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6301-6311

[7] ENANTIOSELECTIVE PALLADIUM-CATALYZED ALLYLIC ALKYLATION WITH C-2-SYMMETRICAL CHIRAL DIAMINE LIGANDS [J].

KUBOTA, H ;

NAKAJIMA, M ;

KOGA, K .

TETRAHEDRON LETTERS, 1993, 34 (50) :8135-8138

[8]

NOYORI R, 1994, ASYMMETRIC CATALYSIS, P192

[9] CHIRAL SEMICORRINS AND RELATED NITROGEN-HETEROCYCLES AS LIGANDS IN ASYMMETRIC CATALYSIS [J].

PFALTZ, A .

ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (06) :339-345

[10] X-RAY-DIFFRACTION, MULTIDIMENSIONAL NMR-SPECTROSCOPY, AND MM2 ASTERISK CALCULATIONS ON CHIRAL ALLYL COMPLEXES OF PALLADIUM(II) [J].

PREGOSIN, PS ;

RUEGGER, H ;

SALZMANN, R ;

ALBINATI, A ;

LIANZA, F ;

KUNZ, RW .

ORGANOMETALLICS, 1994, 13 (01) :83-90

← 1 2 →