Synthesis and resolution of 2-methyl-Quinazolinap, a new atropisomeric phosphinamine ligand for asymmetric catalysis

被引：46

作者：

Lacey, PM ^{[1
]}

McDonnell, CM ^{[1
]}

Guiry, PJ ^{[1
]}

机构：

[1] Natl Univ Ireland Univ Coll Dublin, Dept Chem, Dublin 4, Ireland

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 14期

关键词：

D O I：

10.1016/S0040-4039(00)00183-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation in a five-step sequence of 2-methyl-Quinazolinap, a new atropisomeric ligand for asymmetric catalysis, is described. Diastereomeric palladacycles derived from racemic ligand and (+)-di-mu-chlorobis[(R)-dimethyl(1-( 1-naphthyl)ethyl)aminato-C-2,N]dipalladium(II) were separated by fractional crystallisation. Displacement of the resolving agent by reaction with DPPE afforded enantiopure 2-methyl-Quinazolinap. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2475 / 2478

页数：4

共 22 条

[1] 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

[2] 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

[3]

[Anonymous], COMPREHENSIVE ASYMME

[4]

BELLER M, 1998, TRANSITION METALS OR

[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] trans-2,5-dialkylpyrrolidinyl-containing phosphinamines.: Synthetic and mechanistic studies in Pd-catalysed asymmetric allylic alkylation [J].

Cahill, JP ;

Cunneen, D ;

Guiry, PJ .

TETRAHEDRON-ASYMMETRY, 1999, 10 (21) :4157-4173

[7] SYNTHESIS OF CHIRAL 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (BINAP) VIA A NOVEL NICKEL-CATALYZED PHOSPHINE INSERTION [J].

CAI, DW ;

PAYACK, JF ;

BENDER, DR ;

HUGHES, DL ;

VERHOEVEN, TR ;

REIDER, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :7180-7181

[8] A DEFINITIVE SYNTHESIS OF 2-[(5-METHYL-S-TRIAZOLO[4,3-C]QUINAZOLIN-3-YL)THIO]-N-BENZYLACETANILIDE AND OTHER REACTIONS OF ITS PRECURSORS [J].

HAND, ES ;

BAKER, DC .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (11) :2570-2577

[9] OPTICALLY-ACTIVE ARSENIC MACROCYCLES - STEREOSPECIFIC SYNTHESES OF ENANTIOMERS AND DIASTEREOMERS OF 14-MEMBERED TRANS-AS2S2 CHELATING MACROCYCLES CONTAINING RESOLVED ASYMMETRIC TERTIARY ARSINE DONORS [J].

KERR, PG ;

LEUNG, PH ;

WILD, SB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (14) :4321-4328

[10] A simple route to a novel enantiomerically pure P-chiral phosphine ligand containing a tertiary amide functional group [J].

Leung, PH ;

Loh, SK ;

Mok, KF ;

White, AJP ;

Williams, DJ .

CHEMICAL COMMUNICATIONS, 1996, (05) :591-592

← 1 2 3 →