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

[11] ENHANCED ENANTIOSELECTIVITY OF AN ENZYMATIC-REACTION BY THE SULFUR FUNCTIONAL-GROUP - A SIMPLE PREPARATION OF OPTICALLY-ACTIVE BETA-HYDROXY NITRILES USING A LIPASE [J].

ITOH, T ;

TAKAGI, Y ;

NISHIYAMA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1521-1524

[12] PREPARATION OF OPTICALLY PURE ALPHA-ALKYL BETA-HYDROXY NITRILES BY THE BAKERS-YEAST REDUCTION [J].

ITOH, TY ;

FUKUDA, T ;

FUJISAWA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (12) :3851-3855

[13] APRIORI P-KAPPA-A CALCULATIONS AND THE HYDRATION OF ORGANIC-ANIONS [J].

JORGENSEN, WL ;

BRIGGS, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4190-4197

[14] STRUCTURES AND ENERGIES OF THE LITHIUM, SODIUM, AND MAGNESIUM DERIVATIVES OF THE ANIONS CH2CN- AND CH2NC- - SOLVATION AND AGGREGATION OF THE LITHIUM SPECIES [J].

KANETI, J ;

SCHLEYER, PV ;

CLARK, T ;

KOS, AJ ;

SPITZNAGEL, GW ;

ANDRADE, JG ;

MOFFAT, JB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (07) :1481-1492

[15]

KASATKIN AN, 1990, J ORG CHEM USSR, V26, P1037

[16] ALKYLIRON AND ALKYLCOBALT REAGENTS .4. ALDEHYDE-SELECTIVE CYANOALKYLATION WITH CYANOALKYL DERIVATIVES OF IRON(II) AND OTHER TRANSITION-METALS [J].

KAUFFMANN, T ;

KIEPER, H ;

PIEPER, H .

CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (04) :899-905

[17] CARBON ACIDITY -70- EQUILIBRIUM ION-PAIR ACIDITIES IN TETRAHYDROFURAN OF BENZYLIC CARBON ACIDS STABILIZED BY AN ADJACENT CYANO, CARBOALKOXY, AND SULFONYL SUBSTITUENT - DELOCALIZATION AND AGGREGATION OF ION-PAIRS [J].

KAUFMAN, MJ ;

GRONERT, S ;

BORS, DA ;

STREITWIESER, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (02) :602-603

[18]

KIM BM, 1991, COMPREHENSIVE ORGANI, V2

[19] A WATER-COMPLEXED ORGANOLITHIUM COMPOUND - [LICH(CN)2.H2O.TMEDA]-INFINITY [J].

LAMBERT, C ;

SCHLEYER, PV ;

PIEPER, U ;

STALKE, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (01) :77-79

[20] ENANTIOSELECTIVE DIASTEREOSPECIFIC SYNTHESIS OF ANTI-ALPHA-ALKYL-BETA-HYDROXY ESTERS THROUGH CUPRATE OPENING OF GLYCIDIC ESTERS [J].

MULZER, J ;

LAMMER, O .

CHEMISCHE BERICHTE-RECUEIL, 1986, 119 (07) :2178-2190

← 1 2 3 →