ENANTIOSELECTIVE PREPARATION OF POLYFUNCTIONAL SECONDARY ALLYLIC ALCOHOLS USING FUNCTIONALIZED DIALKYLZINCS PREPARED BY A COPPER(I) CATALYZED IODINE-ZINC EXCHANGE-REACTION

被引：83

作者：

ROZEMA, MJ ^{[1
]}

EISENBERG, C ^{[1
]}

LUTJENS, H ^{[1
]}

OSTWALD, R ^{[1
]}

BELYK, K ^{[1
]}

KNOCHEL, P ^{[1
]}

机构：

[1] UNIV MARBURG,FACHBEREICH CHEM,HANS MEERWEIN ST,W-3550 MARBURG,GERMANY

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 19期

关键词：

D O I：

10.1016/S0040-4039(00)93393-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic amounts of Cu(I) salts considerably facilitate the iodine-zinc exchange reaction leading to polyfunctional dialkylzincs. The catalytic asymmetric addition of these zinc reagents to a wide range of alpha,beta-unsaturated aldehydes provides polyfunctional allylic alcohols with a high enantioselectivity.

引用

页码：3115 / 3118

页数：4

共 17 条

[1] 1ST APPLICATION OF ATTRACTIVE INTRAMOLECULAR INTERACTIONS TO THE DESIGN OF CHIRAL CATALYSTS FOR HIGHLY ENANTIOSELECTIVE DIELS-ALDER REACTIONS [J].

COREY, EJ ;

LOH, TP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8966-8967

[2] TOTAL SYNTHESIS OF (+/-)-FUMAGILLIN [J].

COREY, EJ ;

SNIDER, BB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (07) :2549-&

[3] GAMMA-TRIBUTYLSTANNYL-BETA-METALATED ACROLEIN - A VERSATILE SYNTHON [J].

MAREK, I ;

ALEXAKIS, A ;

NORMANT, JF .

TETRAHEDRON LETTERS, 1991, 32 (44) :6337-6340

[4]

NOYORI R, 1991, ANGEW CHEM INT EDIT, V30, P1321

[5] ENANTIOSELECTIVE ADDITION OF (Z)-ALKENYLZINC AND (E)-ALKENYLZINC BROMIDES TO ALDEHYDES - ASYMMETRIC-SYNTHESIS OF SEC-ALLYLALCOHOLS [J].

OPPOLZER, W ;

RADINOV, RN .

TETRAHEDRON LETTERS, 1991, 32 (41) :5777-5780

[6] CATALYTIC ASYMMETRIC-SYNTHESIS OF SECONDARY (E)-ALLYL ALCOHOLS FROM ACETYLENES AND ALDEHYDES VIA (1-ALKENYL)ZINC INTERMEDIATES - PRELIMINARY COMMUNICATION [J].

OPPOLZER, W ;

RADINOV, RN .

HELVETICA CHIMICA ACTA, 1992, 75 (01) :170-173

[7] ENANTIOSELECTIVE SYNTHESIS OF SEC-ALLYLALCOHOLS BY CATALYTIC ASYMMETRIC ADDITION OF DIVINYLZINC TO ALDEHYDES [J].

OPPOLZER, W ;

RADINOV, RN .

TETRAHEDRON LETTERS, 1988, 29 (44) :5645-5648

[8]

PAARKER DJ, 1983, J CHEM SOC P2, P83

[9] ENANTIOSELECTIVE SYNTHESIS OF THE TOP HALF OF TETRONOLIDE [J].

ROUSH, WR ;

KOYAMA, K .

TETRAHEDRON LETTERS, 1992, 33 (42) :6227-6230

[10] PREPARATION OF FUNCTIONALIZED DIALKYLZINC REAGENTS VIA AN IODINE ZINC EXCHANGE-REACTION - HIGHLY ENANTIOSELECTIVE SYNTHESIS OF FUNCTIONALIZED SECONDARY ALCOHOLS [J].

ROZEMA, MJ ;

SIDDURI, A ;

KNOCHEL, P .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :1956-1958

← 1 2 →