Trimethylsilylcyanation of aromatic aldehydes catalyzed by Pybox-AlCl3 complex

被引：54

作者：

Iovel, I

Popelis, Y

Fleisher, M

Lukevics, E

机构：

[1] Latvian Inst. of Organic Synthesis, Riga

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 08期

关键词：

D O I：

10.1016/S0957-4166(97)00100-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A series of aromatic and heterocyclic cyanohydrins and their O-silyl ethers have been synthesized by trimethylsilylcyanation of aldehydes using a catalyst generated in situ from (S,S)-2,6-bis(4'-isopropyloxazolin-2'-yl)pyridine (Pybox) with AlCl3. Mandelonitrile was prepared in isolated yield 92% with more than 90% ee. The structure of AlCl3-Pybox complex was studied by means of H-1 NMR and quantum-chemical calculations. (C) 1997 Elsevier Science Ltd.

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页码：1279 / 1285

页数：7

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共 54 条

[1]

ABICO A, 1996, J ORG CHEM, V61, P2264

[2] REACTIONS OF ACYL ANION EQUIVALENTS DERIVED FROM CYANOHYDRINS, PROTECTED CYANOHYDRINS AND ALPHA-DIALKYLAMINONITRILES [J].

ALBRIGHT, JD .

TETRAHEDRON, 1983, 39 (20) :3207-3233

[3] Asymmetric trimethylsilylcyanation of aldehydes catalyzed by chiral (salen)Ti(IV) complexes. [J].

Belokon, Y ;

Ikonnikov, N ;

Moscalenko, M ;

North, M ;

Orlova, S ;

Tararov, V ;

Yashkina, L .

TETRAHEDRON-ASYMMETRY, 1996, 7 (03) :851-855

[4] ENANTIOSELECTIVE TRIMETHYLSILYLCYANATION OF ALDEHYDES [J].

BOLM, C ;

MULLER, P .

TETRAHEDRON LETTERS, 1995, 36 (10) :1625-1628

[5] SYNTHETIC APPLICATIONS OF OPTICALLY-ACTIVE CYANOHYDRINS - ENANTIOSELECTIVE SYNTHESES OF THE HYDROXYAMIDES TEMBAMIDE AND AEGELINE, THE CARDIAC DRUG DENOPAMINE, AND SOME ANALOGS OF THE BRONCHODILATOR SALBUTAMOL [J].

BROWN, RFC ;

DONOHUE, AC ;

JACKSON, WR ;

MCCARTHY, TD .

TETRAHEDRON, 1994, 50 (48) :13739-13752

[6] PREPARATION OF 1,2 AMINOLS FROM CYANOHYDRINS VIA N-DIISOBUTYLALUMINIUM IMINES [J].

CAINELLI, G ;

PANUNZIO, M ;

CONTENTO, M ;

GIACOMINI, D ;

MEZZINA, E ;

GIOVAGNOLI, D .

TETRAHEDRON, 1993, 49 (18) :3809-3826

[7] GROUND-STATE MOLECULES .59. MNDO STUDY OF SN2 REACTIONS AND RELATED PROCESSES [J].

CARRION, F ;

DEWAR, MJS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (12) :3531-3539

[8] MNDO CALCULATIONS FOR COMPOUNDS CONTAINING ALUMINUM AND BORON [J].

DAVIS, LP ;

GUIDRY, RM ;

WILLIAMS, JR ;

DEWAR, MJS ;

RZEPA, HS .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1981, 2 (04) :433-445

[9] TRIMETHYLSILYL CYANIDE - REAGENT FOR UMPOLUNG .1. NUCLEOPHILIC ACYLATION OF ALKYLATING REAGENTS WITH AROMATIC AND HETEROAROMATIC ALDEHYDES [J].

DEUCHERT, K ;

HERTENSTEIN, U ;

HUNIG, S ;

WEHNER, G .

CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (06) :2045-2061

[10] GROUND-STATES OF MOLECULES .39. MNDO RESULTS FOR MOLECULES CONTAINING HYDROGEN, CARBON, NITROGEN, AND OXYGEN [J].

DEWAR, MJS ;

THIEL, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (15) :4907-4917

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