A MECHANISTICALLY DESIGNED MONO-CINCHONA ALKALOID IS AN EXCELLENT CATALYST FOR THE ENANTIOSELECTIVE DIHYDROXYLATION OF OLEFINS

被引：43

作者：

COREY, EJ

NOE, MC

GROGAN, MJ

机构：

[1] Department of Chemistry, Harvard University, Cambridge

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 35期

关键词：

D O I：

10.1016/S0040-4039(00)78237-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

On the basis of ideas recently advanced regarding the origin of enantioselectivity in the OsO4-promoted dihydroxylation of olefins catalyzed by bis-cinchona alkaloid derivatives such as 1, specifically strong evidence for reaction via transition stale assembly 2, the mono-quinidine derivative 3 was selected as a promising catalytic ligand. The experimental observation of high enantioselectivity promoted by 3 provides additional evidence in favor of transition-state 2.

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页码：6427 / 6430

页数：4

相关论文

共 11 条

[1] X-RAY MOLECULAR-STRUCTURE OF ASYMMETRICALLY BRIDGED ESTER COMPLEX DI-MU-OXO-BIS[(CYCLOHEXANE-1,2-DIOLATO)OXO(QUINUCLIDINE)OSMIUM(VI)], [OSO2(O2C6H10)(C7H13N)]2 [J].

CARTWRIGHT, BA ;

GRIFFITH, WP ;

SCHRODER, M ;

SKAPSKI, AC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (19) :853-854

[2] RIGID AND HIGHLY ENANTIOSELECTIVE CATALYST FOR THE DIHYDROXYLATION OF OLEFINS USING OSMIUM TETRAOXIDE CLARIFIES THE ORIGIN OF ENANTIOSPECIFICITY [J].

COREY, EJ ;

NOE, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (26) :12579-12580

[3] A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S ;

CHEN, CP ;

SINGH, VK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7925-7926

[4] X-RAY CRYSTALLOGRAPHIC STUDIES PROVIDE ADDITIONAL EVIDENCE THAT AN ENZYME-LIKE BINDING POCKET IS CRUCIAL TO THE ENANTIOSELECTIVE DIHYDROXYLATION OF OLEFINS BY OSO4-BIS-CINCHONA ALKALOID COMPLEXES [J].

COREY, EJ ;

NOE, MC ;

SARSHAR, S .

TETRAHEDRON LETTERS, 1994, 35 (18) :2861-2864

[5] CONFORMATIONAL STUDY OF CINCHONA ALKALOIDS - A COMBINED NMR, MOLECULAR MECHANICS, AND X-RAY APPROACH [J].

DIJKSTRA, GDH ;

KELLOGG, RM ;

WYNBERG, H ;

SVENDSEN, JS ;

MARKO, I ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) :8069-8076

[6]

GOLDEN R, 1972, J AM CHEM SOC, V94, P3080, DOI 10.1021/ja00764a032

[7] THE ORIGIN OF HIGH ENANTIOSELECTIVITY IN THE DIHYDROXYLATION OF OLEFINS USING OSMIUM TETRAOXIDE AND CINCHONA ALKALOID CATALYSTS [J].

KOLB, HC ;

ANDERSSON, PG ;

BENNANI, YL ;

CRISPINO, GA ;

JEONG, KS ;

KWONG, HL ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (25) :12226-12227

[8] TOWARD AN UNDERSTANDING OF THE HIGH ENANTIOSELECTIVITY IN THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION (AD) .1. KINETICS [J].

KOLB, HC ;

ANDERSSON, PG ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (04) :1278-1291

[9] CATALYTIC ASYMMETRIC DIHYDROXYLATION OF TETRASUBSTITUTED OLEFINS [J].

MORIKAWA, K ;

PARK, J ;

ANDERSSON, PG ;

HASHIYAMA, T ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) :8463-8464

[10] NEW CLASS OF MIXED CUPRATE(I) REAGENTS, HET(R)CULI, WHICH ALLOW SELECTIVE ALKYL GROUP TRANSFER [J].

POSNER, GH ;

WHITTEN, CE ;

STERLING, JJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (23) :7788-7800