VANADIUM(II) PROMOTED DIASTEREOSELECTIVE AND ENANTIOSELECTIVE INTERMOLECULAR PINACOL CROSS COUPLING

被引：22

作者：

ANNUNZIATA, R ^{[1
]}

CINQUINI, M ^{[1
]}

COZZI, F ^{[1
]}

GIARONI, P ^{[1
]}

机构：

[1] DIPARTIMENTO CHIM ORGAN & IND,MILAN,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1990年 / 1卷 / 06期

关键词：

D O I：

10.1016/0957-4166(90)90032-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The cross coupling reaction promoted by [V2Cl3(THF)6]2[Zn2Cl6] of some aliphatic aldehydes with an aromatic aldehyde bearing a chiral auxiliary occurs in a stereocontrolled fashion to give syn 1,2- diols in diastereoisomeric ratios up to 91:9 and enantiomeric excesses up to 84%. © 1990.

引用

收藏

页码：355 / 358

页数：4

相关论文

共 15 条

[1] ENANTIOFACE-DIFFERENTIATING ADDITION OF A CHIRAL ARYLLITHIUM REAGENT TO ALDEHYDES [J].

ASAMI, M ;

MUKAIYAMA, T .

CHEMISTRY LETTERS, 1980, (01) :17-20

[2] REDUCTION OF ORTHO-HYDROXYBENZALDEHYDES BY AQUEOUS TITANIUM TRICHLORIDE - A NEW ROUTE TO 2-(BENZOFURAN-2-YL)PHENOLS [J].

CLERICI, A ;

PORTA, O ;

ARNONE, A .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) :1240-1248

[3] ENANTIOSELECTIVE VICINAL HYDROXYLATION OF TERMINAL AND E-1,2-DISUBSTITUTED OLEFINS BY A CHIRAL COMPLEX OF OSMIUM TETRAOXIDE - AN EFFECTIVE CONTROLLER SYSTEM AND A RATIONAL MECHANISTIC MODEL [J].

COREY, EJ ;

JARDINE, PD ;

VIRGIL, S ;

YUEN, PW ;

CONNELL, RD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) :9243-9244

[4] 2 COMPOUNDS CONTAINING THE TRIS(MU-CHLORO)HEXAKIS(TETRAHYDROFURAN)DIVANADIUM(II) CATION - PREPARATION, STRUCTURES, AND SPECTROSCOPIC CHARACTERIZATION [J].

COTTON, FA ;

DURAJ, SA ;

ROTH, WJ .

INORGANIC CHEMISTRY, 1985, 24 (06) :913-917

[5]

Enders D., 1987, ORG SYNTH, V65, P173

[6] INTERMOLECULAR PINACOL CROSS COUPLING OF ELECTRONICALLY SIMILAR ALDEHYDES - AN EFFICIENT AND STEREOSELECTIVE SYNTHESIS OF 1,2-DIOLS EMPLOYING A PRACTICAL VANADIUM(II) REAGENT [J].

FREUDENBERGER, JH ;

KONRADI, AW ;

PEDERSEN, SF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) :8014-8016

[7] NUCLEOPHILIC-ADDITION OF LANTHANOID METAL UMPOLED DIARYL KETONES TO ELECTROPHILES [J].

HOU, ZM ;

TAKAMINE, K ;

AOKI, O ;

SHIRAISHI, H ;

FUJIWARA, Y ;

TANIGUCHI, H .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) :6077-6084

[8]

MANZER LE, 1982, INORG SYN, V21, P135

[9] CARBONYL-COUPLING REACTIONS USING LOW-VALENT TITANIUM [J].

MCMURRY, JE .

CHEMICAL REVIEWS, 1989, 89 (07) :1513-1524

[10] ASYMMETRIC OXIDATION OF OLEFINS WITH OSMIUM-TETROXIDE [J].

NAKAJIMA, M ;

TOMIOKA, K ;

KOGA, K .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1989, 47 (10) :878-888