IRON-PROMOTED, REGIOSELECTIVE AND STEREOSELECTIVE ALLYLIC SUBSTITUTIONS FOR THE SYNTHESIS OF ALKENYL SULFONES SUBSTITUTED AT C-3

被引：39

作者：

ENDERS, D

JANDELEIT, B

RAABE, G

机构：

[1] Institut Für Organische Chemie, Technischen Hochschule Aachen, D-52074

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1994年 / 33卷 / 19期

关键词：

D O I：

10.1002/anie.199419491

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Almost complete transfer of chirality is observed in the nucleophilic addition of various carbon and nitrogen nucleophiles (Nu) to the highly enantiomerically enriched 1‐phenylsulfonyl‐substituted (η3‐allyl)tetracarbonyliron(1+) tetrafluoroborate with planar chirality (1; de, ee > 98%). Oxidative decomplexation yields alkenyl phenyl sulfones 2 with a range of subtituents at C‐3 and high enantiomeric purity (ee ≥ 96%). (Figure Presented.) Copyright © 1994 by VCH Verlagsgesellschaft mbH, Germany

引用

收藏

页码：1949 / 1951

页数：3

相关论文

共 63 条

[21]

HALL SR, 1992, XTAL 3 2 REFRENCE MA

[22] STRUCTURES OF TETRACARBONYL(2-3-ETA-MALEIC ACID)IRON, CIS-[FE(C4H4O4)(CO)4](1) AND TETRACARBONYL(2-3-ETA-FUMARIC ACID)IRON, TRANS-[FE(C4H4O4)(CO)4](2) [J].

HSIOU, Y ;

WANG, Y ;

LIU, LK .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1989, 45 :721-724

[23] SULFINYL-CONTROLLED FORMATION OF DIASTEREOISOMERICALLY PURE TRICARBONYL(OXADIENE)IRON(0) COMPLEXES AND A DIASTEREOISOMERICALLY PURE TETRACARBONYL(ALKENE)IRON(0) COMPLEX [J].

IBBOTSON, A ;

DOSREIS, ACR ;

SABERI, SP ;

SLAWIN, AMZ ;

THOMAS, SE ;

TUSTIN, GJ ;

WILLIAMS, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (10) :1251-1259

[24]

IBUKA T, 1994, ANGEW CHEM INT EDIT, V33, P652, DOI 10.1002/anie.199406521

[25] REMARKABLE DIFFERENCE IN REACTIVITY OF ORDINARY VINYLCOPPER REAGENTS AND VINYLZINC HALIDE CONTAINING A COPPER SALT TOWARDS GAMMA-MESYLOXY-ALPHA, BETA-ENOATES - SYNTHESIS OF HOMOCHIRAL 1,4-DIENES [J].

IBUKA, T ;

NAKAI, K ;

HABASHITA, H ;

BESSHO, K ;

FUJII, N ;

CHOUNAN, Y ;

YAMAMOTO, Y .

TETRAHEDRON, 1993, 49 (42) :9479-9488

[26]

IBUKA T, 1992, SYNLETT, P769

[27] SYN-S(N)2' PATHWAY IN THE REACTION OF CERTAIN GAMMA-(MESYLOXY) ALPHA, BETA-ENOATES WITH RCU(CN)MGX.BF3 REAGENTS - IMPORTANCE OF MGX AND BULKY R-GROUP UPON THE DIASTEREOSELECTIVITY [J].

IBUKA, T ;

TAGA, T ;

HABASHITA, H ;

NAKAI, K ;

TAMAMURA, H ;

FUJII, N ;

CHOUNAN, Y ;

NEMOTO, H ;

YAMAMOTO, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1207-1214

[28]

IBUKA T, 1994, ANGEW CHEM, V106, P693

[29] NOVEL SYNTHESES OF THE CARBAPENEM KEY INTERMEDIATES, (3R,4R)-4-ACETOXY-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-2-AZETIDINONE AND (3S,4R)-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-4-CARBOXYMETHYL-2-AZETIDINONE, FROM (S)-ETHYL LACTATE [J].

ITO, Y ;

KOBAYASHI, Y ;

KAWABATA, T ;

TAKASE, M ;

TERASHIMA, S .

TETRAHEDRON, 1989, 45 (18) :5767-5790

[30] NUCLEOPHILIC-ADDITION TO COORDINATED CYCLIC PI-HYDROCARBONS - MECHANISTIC AND SYNTHETIC STUDIES [J].

KANEMAGUIRE, LAP ;

HONIG, ED ;

SWEIGART, DA .

CHEMICAL REVIEWS, 1984, 84 (06) :525-543

← 1 2 3 4 5 6 7 →