Synthesis and resolution of benzylisopropylphenylphosphine a monodentate P-chiral ligand

被引：35

作者：

Albert, J ^{[1
]}

Bosque, R ^{[1
]}

Cadena, JM ^{[1
]}

Granell, JR ^{[1
]}

Muller, G ^{[1
]}

Ordinas, JI ^{[1
]}

机构：

[1] Univ Barcelona, Dept Quim Inorgan, E-08028 Barcelona, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 16期

关键词：

D O I：

10.1016/S0957-4166(00)00300-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis of benzylisopropylphenylphosphine by reaction between the benzylphenylphosphide anion and isopropyl chloride and its subsequent resolution by means of an optically active palladium metallacycle is reported. The synthesis of the organometallic complex [Pd(eta(3)-2-MeC3H4)Cl((PBnPrPh)-Pr-i)] is also described, as well as the assignment of the absolute configuration of the coordinated phosphine by mono- and bidimensional proton NMR spectra, using the homochiral palladacycle as a reference point. In order to estimate the height of the energy barrier corresponding to the rotation of the phosphine ligand around the Pd-P bond, several calculations were performed at the semiempirical PM3(tm) level. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3335 / 3343

页数：9

共 70 条

[1] OPTICALLY-ACTIVE EXOCYCLIC CYCLOPALLADATED DERIVATIVES OF BENZYLIDENE-(R)-(1-PHENYLETHYL)AMINES - SYNTHESES AND X-RAY MOLECULAR-STRUCTURES OF [PD(2-((E)-(R)-CHMEN=CH-2',6'-CL2C6H3)C6H4)CL(PPH(3))] AND [PD(2-((Z)-(R)-CHMEN=CH-2',6'-F2C6H3)C6H4)I(PPH(3))] [J].

ALBERT, J ;

GRANELL, J ;

SALES, J ;

FONTBARDIA, M ;

SOLANS, X .

ORGANOMETALLICS, 1995, 14 (03) :1393-1404

[2] Cyclopalladation of the primary amine (R)-(+)-1-(1-naphthyl)ethylamine: A new resolving agent for monodentate phosphines [J].

Albert, J ;

Cadena, JM ;

Granell, J .

TETRAHEDRON-ASYMMETRY, 1997, 8 (07) :991-994

[3] An approach to the synthesis of platinum complexes containing chiral monodentate phosphines with simultaneous regeneration of the resolving agent [J].

Albert, J ;

Granell, J ;

Minguez, J ;

Muller, G ;

Sainz, D ;

Valerga, P .

ORGANOMETALLICS, 1997, 16 (15) :3561-3564

[4] Resolution of benzylcyclohexylphenylphosphine by palladium(II)-amine metallacycles.: A new ligand for asymmetric hydrovinylation [J].

Albert, J ;

Cadena, JM ;

Granell, J ;

Muller, G ;

Ordinas, JI ;

Panyella, D ;

Puerta, C ;

Sañudo, C ;

Valerga, P .

ORGANOMETALLICS, 1999, 18 (17) :3511-3518

[5] SYNTHESIS AND RESOLUTION OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE - A P-N CHELATING LIGAND FOR ASYMMETRIC CATALYSIS [J].

ALCOCK, NW ;

BROWN, JM ;

HULMES, DI .

TETRAHEDRON-ASYMMETRY, 1993, 4 (04) :743-756

[6] CONTRASTING BEHAVIOR OF RELATED PALLADIUM COMPLEX-DERIVED RESOLVING AGENTS - 8-H CONFORMATIONAL LOCKING OF THE 1-NAPHTHYL SIDE-CHAIN [J].

ALCOCK, NW ;

HULMES, DI ;

BROWN, JM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (03) :395-397

[7]

[Anonymous], COMPREHENSIVE ASYMME

[8]

AW B, 1997, INORG CHEM, V37, P2138

[9] NMR assignment of absolute configuration of a P-chiral diphosphine and mechanics of its stereoselective formation [J].

Aw, BH ;

Selvaratnam, S ;

Leung, PH ;

Rees, NH ;

McFarlane, W .

TETRAHEDRON-ASYMMETRY, 1996, 7 (06) :1753-1762

[10] SYNTHESIS, RESOLUTION AND REACTIONS OF (+/-)-(2-AMINO-PHENYL)METHYLPHENYLPHOSPHINE - CRYSTAL AND MOLECULAR-STRUCTURE OF (R-ASTERISK, R-ASTERISK, S-ASTERISK, R-ASTERISK)-(+/-)-(1,3-BIS([2-(METHYLPHENYL-PHOSPHINO)PHENYL]AMINO)PROPANE)NICKEL(II) PERCHLORATE [J].

BARCLAY, CE ;

DEEBLE, G ;

DOYLE, RJ ;

ELIX, SA ;

SALEM, G ;

JONES, TL ;

WILD, SB ;

WILLIS, AC .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1995, (01) :57-65

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