Synthesis and resolution of quinazolinone atropisomeric phosphine ligands

被引：90

作者：

Dai, XD ^{[1
]}

Wong, A ^{[1
]}

Virgil, SC ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 08期

关键词：

D O I：

10.1021/jo972105z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The syntheses of 2-methyl-3-[2'-(diphenylphosphino)phenyl]-4(3H)-quinazolinone (MPQ, 1a) and methyl-substituted analogues were achieved in good yield by coupling N-acetylanthranilic acid with the corresponding phosphinoanilines. Resolution of ligand 1b was achieved using (-)-di-mu-chlorobis[(S)-dimethyl-( 1-phenylethyl)aminato-C-2,N]dipalladium(II) (5). The resulting crystalline complex (S,R)-6 served to unambiguously assign the absolute configuration of antipode (R)-(-)-1b. A practical resolution of this series of ligands 1a-c was accomplished using the (benzenesulfonyl)hydrazone derivative of camphorsulfonic acid (7) as a resolving agent.

引用

页码：2597 / 2600

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].