ZIRCONIUM-MEDIATED DIASTEREOSELECTIVE COUPLING REACTIONS OF CHIRAL ALDIMINE - REMARKABLE TEMPERATURE-DEPENDENCE OF CHIRAL INDUCTION

被引：52

作者：

ITO, H ^{[1
]}

TAGUCHI, T ^{[1
]}

HANZAWA, Y ^{[1
]}

机构：

[1] TOKYO COLL PHARM,1432-1 HORINOUCHI,HACHIOJI,TOKYO 19203,JAPAN

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 31期

关键词：

ZIRCONOCENE; ZIRCONAAZIRIDINE; CHIRAL ALDIMINE; TEMPERATURE EFFECT; AMINO ALCOHOL DERIVATIVES;

D O I：

10.1016/S0040-4039(00)60112-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Zr-Mediated coupling reactions of aldehyde with chiral aldimine which is derived from benzaldehyde and (R)-phenylglycinol methyl ether showed a remarkable temperature effect on the sense of chiral induction to yield amino alcohol derivatives with high diastereoselectivities.

引用

页码：4469 / 4472

页数：4

共 17 条

[1] STEREOCHEMISTRY OF IMINO GROUP REDUCTION .2. SYNTHESIS AND ASSIGNMENT OF CONFIGURATION OF SOME N-(1-PHENYLETHYL)-1,2-DIARYL-2-AMINOETHANOLS [J].

ALCAIDE, B ;

DELAPRADILLA, RF ;

LOPEZMARDOMINGO, C ;

PEREZOSSORIO, R ;

PLUMET, J .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (16) :3234-3238

[2] GROUP-4 METAL-COMPLEXES OF BENZYNES, CYCLOALKYNES, ACYCLIC ALKYNES, AND ALKENES [J].

BUCHWALD, SL ;

NIELSEN, RB .

CHEMICAL REVIEWS, 1988, 88 (07) :1047-1058

[3] ZIRCONOCENE COMPLEXES OF IMINES - GENERAL-SYNTHESIS, STRUCTURE, REACTIVITY, AND INSITU GENERATION TO PREPARE GEOMETRICALLY PURE ALLYLIC AMINES [J].

BUCHWALD, SL ;

WATSON, BT ;

WANNAMAKER, MW ;

DEWAN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4486-4494

[4]

BUCHWALD SL, 1989, CHEM SCRIPTA, V29, P417

[5] SEQUENTIAL PI-LIGAND EXCHANGE FROM METALLACYCLOPENTANES - SYNTHESIS AND STRUCTURE OF 1,1-BIS(CYCLOPENTADIENYL)-2,3-DIPHENYL-1-HAFNACYCLOPENT-2-ENE [J].

ERKER, G ;

DORF, U ;

RHEINGOLD, AL .

ORGANOMETALLICS, 1988, 7 (01) :138-143

[6] ENANTIOSELECTIVE, ZIRCONIUM-MEDIATED SYNTHESIS OF ALLYLIC AMINES [J].

GROSSMAN, RB ;

DAVIS, WM ;

BUCHWALD, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (06) :2321-2322

[7] ELECTRONIC CONTROL OF REGIOSELECTIVITY IN COUPLING REACTIONS OF SIME3-SUBSTITUTED ALKENES WITH CP2ZR(ETA-2(N,C2)-6-PHENYLPYRIDYL)(THF)+ [J].

GURAM, AS ;

JORDAN, RF .

ORGANOMETALLICS, 1990, 9 (08) :2190-2192

[8] STEREOSELECTIVE FORMATION OF CARBON CARBON BONDS THROUGH METAL CATALYSIS - THE ZIRCONIUM-CATALYZED ETHYLMAGNESATION REACTION [J].

HOVEYDA, AH ;

XU, ZM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) :5079-5080

[9] STEREOSELECTIVE ZIRCONIUM-CATALYZED ETHYLMAGNESATION OF HOMOALLYLIC ALCOHOLS AND ETHERS - THE INFLUENCE OF INTERNAL LEWIS-BASES ON SUBSTRATE REACTIVITY [J].

HOVEYDA, AH ;

XU, ZM ;

MORKEN, JP ;

HOURI, AF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8950-8952

[10] BICYCLIZATION OF UNSATURATED HYDRAZONES MEDIATED BY ZIRCONOCENE COMPLEXES - A NEW ANNULATION STRATEGY BASED ON THE REDUCTIVE COCYCLIZATION OF AZOMETHINE LINKAGES WITH CARBON CARBON MULTIPLE BONDS [J].

JENSEN, M ;

LIVINGHOUSE, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4495-4496

← 1 2 →