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

被引：304

作者：

ALCOCK, NW ^{[1
]}

BROWN, JM ^{[1
]}

HULMES, DI ^{[1
]}

机构：

[1] DYSON PERRINS LAB,OXFORD OX1 3QY,ENGLAND

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 04期

关键词：

D O I：

10.1016/S0957-4166(00)80183-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A multistep synthesis resulting in a good yield of the title compound has been developed based on the Pd-catalysed coupling of 1-chloroisoquinoline and 2-methoxy-1-naphthylboronic acid (5). The product is converted into the corresponding tfifluoromethanesulphonate (10) by successive demethylation and treatment with (CF3CO)2O, followed by a further Pd-catalysed coupling with Ph2P(O)H. The resulting phosphine oxide (11) was cleanly reduced with HSiCl3. Resolution of the phosphinamine (4) was carried out with the Pd complex derived from (R)-(+)-dimethyl(1-(1-naphthyl)ethyl)amine and PdCl2; the diastereomers were of different stabilities and solubilities and were therefore readily separated. The resolved phosphinamine, [alpha]D22 +/- 153 (c = 1, CHCl3), was enantiomerically stable on heating to 65-degrees-C for 24h. X-ray crystal structures of the adduct (16) and the Pd dimer (7) isolated during the initial coupling reaction are presented.

引用

页码：743 / 756

页数：14

共 40 条

[31] RESOLUTIONS USING METAL-COMPLEXES - SYNTHESIS, SEPARATION INTO DIASTEREOISOMERS, AND RESOLUTION OF ORTHO-PHENYLENEBIS(METHYLPHENYLPHOSPHINE) USING PALLADIUM COMPLEXES CONTAINING OPTICALLY-ACTIVE ORTHO-METALLATED DIMETHYL(ALPHA-METHYLBENZYL)AMINES [J].