INFLUENCE OF 1,4-BIS(DIPHENYLPHOSPHINO)BUTANE ON THE HYDROFORMYLATION OF ALPHA,BETA-UNSATURATED ESTERS CATALYZED BY ZWITTERIONIC, CATIONIC, AND NEUTRAL RHODIUM(I) COMPLEXES - THE ASYMMETRIC HYDROFORMYLATION OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONE

被引：49

作者：

LEE, CW ^{[1
]}

ALPER, H ^{[1
]}

机构：

[1] UNIV OTTAWA,DEPT CHEM,OTTAWA,ON K1N 6N5,CANADA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 03期

关键词：

D O I：

10.1021/jo00108a007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An investigation was made of the effect of 1,4-bis(diphenylphosphino)butane (dppb) on the regioselectivity of the hydroformylation of alpha,beta>-unsaturated esters with synthesis gas, catalyzed by rhodium(I) complexes. Excellent regioselectivity was obtained when dppb was added as a ligand for the reaction of methyl acrylate and alpha-methylene-gamma-butyrolactone with synthesis gas. However, it inhibits the reaction when methyl methacrylate is used as the substrate. The asymmetric hydroformylation of alpha-methylene-gamma-butyrolactone using [Rh(1,5-hd)(phen)]Cl-+(-) as the catalyst and (R)-BINAP as the chiral ligand (6:1 ratio of(R)-BINAP/Rh) gave an aldehydic lactone, containing a quaternary chiral center, in up to 37% ee.

引用

页码：499 / 503

页数：5

共 32 条

[1] EXCELLENT REGIOCHEMICAL CONTROL IN THE HYDROFORMYLATION OF ALPHA,BETA-UNSATURATED ESTERS CATALYZED BY ZWITTERIONIC RHODIUM COMPLEXES AND 1,4-BIS(DIPHENYLPHOSPHINO)BUTANE [J].