2,3-ANTI SELECTIVE ALDOL REACTION OF PHENYLACETONITRILE

被引：23

作者：

CARLIER, PR

LO, KM

机构：

[1] Department of Chemistry, Hong Kong University of Science and Technology, Kowloon, Clear Water Bay

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 15期

关键词：

D O I：

10.1021/jo00094a011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereoselective (3.3:1 to >50:1) aldol reaction of nitriles and aldehydes is reported for the first time; concentration studies and the observed 2,3-anti selectivity suggest the intermediacy of a monomeric N-lithiated nitrile anion.

引用

页码：4053 / 4055

页数：3

共 27 条

[1] CHARGE MAPPING IN CARBANIONS - WEAK CHARGE DEMAND OF THE CYANO GROUP AS ASSESSED FROM A C-13 NMR-STUDY OF CARBANIONS OF ALPHA-ACTIVATED ACETONITRILES AND PHENYLACETONITRILES - BREAKDOWN OF A MYTH [J].

ABBOTTO, A ;

BRADAMANTE, S ;

PAGANI, GA .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) :449-455

[2] CRYSTAL-STRUCTURE OF [ALPHA-CYANOISOPROPYL-SODIUM . TETRAMETHYLENEDIAMINE)4] - HOW COORDINATION EXPANSION FROM LI TO NA CENTERS CAN INCREASE THE AGGREGATION STATE OF AN ALPHA-NITRILE CARBANION [J].

BARKER, J ;

BARNETT, NDR ;

BARR, D ;

CLEGG, W ;

MULVEY, RE ;

ONEIL, PA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (09) :1366-1368

[3] DEGREE OF AGGREGATION OF ORGANO-LITHIUM COMPOUNDS BY MEANS OF CRYOSCOPY IN TETRAHYDROFURAN [J].

BAUER, W ;

SEEBACH, D .

HELVETICA CHIMICA ACTA, 1984, 67 (07) :1972-1988

[4] X-RAY STRUCTURE DETERMINATION OF [1-CYANO-2,2-DIMETHYLCYCLOPROPYLLITHIUM-TETRAHYDROFURAN]INFINITY - A TETRAHEDRAL ANIONIC ALPHA-CYANO CARBON-ATOM [J].

BOCHE, G ;

HARMS, K ;

MARSCH, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6925-6926

[5] THE STRUCTURE OF LITHIUM COMPOUNDS OF SULFONES, SULFOXIMIDES, SULFOXIDES, THIOETHERS AND 1,3-DITHIANES, NITRILES, NITRO-COMPOUNDS AND HYDRAZONES [J].

BOCHE, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (03) :277-297

[6] STRUCTURAL STUDY AND REACTIVITY OF CARBANIONS IN SOLUTION - PHENYLACETONITRILES AND 3-PYRIDYLACETONITRILES [J].

CROISAT, D ;

SEYDENPENNE, J ;

STRZALKO, T ;

WARTSKI, L ;

CORSET, J ;

FROMENT, F .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) :6435-6447

[7] REGIOCONTROLLED AND STEREOCONTROLLED SYNTHESIS OF ALLENIC AND ACETYLENIC DERIVATIVES - ORGANOTITANIUM AND BORON REAGENTS [J].

FURUTA, K ;

ISHIGURO, M ;

HARUTA, R ;

IKEDA, N ;

YAMAMOTO, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (10) :2768-2776

[8] AN ALDOL-TYPE REACTION OF ACETONITRILES USING DIALKYLBORYL TRIFLATE [J].

HAMANA, H ;

SUGASAWA, T .

CHEMISTRY LETTERS, 1982, (09) :1401-1404

[9]

Heathcock C. H., 1991, COMPREHENSIVE ORGANI, V2

[10] THE CRYSTAL-STRUCTURES OF (LI3(12-CROWN-4)2[HC(CN)2]3), (NA(15-CROWN-5)[HC(CN)2]), AND (NA[N(NBU)4][HC(CN)2]2. THF) [J].

HILLER, W ;

FREY, S ;

STAHLE, J ;

BOCHE, G ;

ZARGES, W ;

HARMS, K ;

MARSCH, M ;

WOLLERT, R ;

DEHNICKE, K .

CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (01) :87-92

← 1 2 3 →