A highly dl-stereoselective pinacolization of aromatic aldehydes mediated by titanium trichloride in dichloromethane

被引：65

作者：

Clerici, A ^{[1
]}

Clerici, L ^{[1
]}

Porta, O ^{[1
]}

机构：

[1] POLITECN MILAN,DIPARTIMENTO CHIM,I-20133 MILAN,ITALY

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 17期

关键词：

D O I：

10.1016/0040-4039(96)00462-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aromatic aldehydes are stereoselectively coupled to dl-hydrobenzoins on treatment with anhydrous TiCl3/CH2Cl2 solution at room temperature. The observed stereochemistry is briefly discussed in term of Ti(IV)-bridging control. (C) 1986 Elsevier Science Ltd.

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页码：3035 / 3038

页数：4

相关论文

共 22 条

[1] ANIONIC ZIRCONAOXIRANES AS NUCLEOPHILIC ALDEHYDE EQUIVALENTS - APPLICATION TO INTERMOLECULAR PINACOL CROSS-COUPLING [J].

ASKHAM, FR ;

CARROLL, KM .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) :7328-7329

[2]

CHAU TH, 1972, TETRAHEDRON LETT, V13, P75

[3] PINACOLIC COUPLING OF AROMATIC-ALDEHYDES AND KETONES PROMOTED BY AQUEOUS TITANIUM TRICHLORIDE IN BASIC-MEDIA [J].

CLERICI, A ;

PORTA, O .

TETRAHEDRON LETTERS, 1982, 23 (34) :3517-3520

[4] REDUCTION OF AROMATIC CARBONYL-COMPOUNDS PROMOTED BY TITANIUM TRICHLORIDE IN BASIC-MEDIA - STEREOCHEMISTRY STUDIES [J].

CLERICI, A ;

PORTA, O .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (01) :76-81

[5] NOVEL REACTIONS OF MONOCYCLOPENTADIENYLTITANIUM(III) DIHALIDES WITH ORGANIC CARBONYL GROUPS [J].

COUTTS, RSP ;

WAILES, PC ;

MARTIN, RL .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 50 (01) :145-151

[6]

DUTHALER RO, 1992, CHEM REV, P813

[7]

FURSTER A, 1988, J CHEM SOC P1, P229

[8] A HIGHLY STEREOSELECTIVE PINACOLIZATION OF AROMATIC AND ALPHA,BETA-UNSATURATED ALDEHYDES MEDIATED BY TITANIUM(III)-MAGNESIUM(II) COMPLEX [J].

HANDA, Y ;

INANAGA, J .

TETRAHEDRON LETTERS, 1987, 28 (46) :5717-5718

[9]

INAMOTO T, 1982, TETRAHEDRON LETT, V23, P1353

[10] SAMARIUM DIBROMIDE, AN EFFICIENT REAGENT FOR THE PINACOL COUPLING REACTIONS [J].

LEBRUN, A ;

NAMY, JL ;

KAGAN, HB .

TETRAHEDRON LETTERS, 1993, 34 (14) :2311-2314