Chiral organometallic reagents .20. An enantiomerically enriched (alpha-phenylselenolalkyl)magnesium compound

被引：19

作者：

Klute, W ^{[1
]}

Kruger, M ^{[1
]}

Hoffmann, RW ^{[1
]}

机构：

[1] UNIV MARBURG,FACHBEREICH CHEM,D-35302 MARBURG,GERMANY

来源：

CHEMISCHE BERICHTE | 1996年 / 129卷 / 06期

关键词：

Grignard reagents; alpha-seleno-substituted; kinetic resolution; racemization;

D O I：

10.1002/cber.19961290607

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

alpha-Selenoalkyl Grignard reagents 2 are chiral. On reaction with the magnesium chelate 3a of alpha w-benzyloxypropionaldehyde they show significant degrees of kinetic resolution, especially when the reactions are run in CH2Cl2. Under these conditions, racemic 2 was resolved by reaction with 0.59 equivalents of 3a at temperatures below -20 degrees C. The remaining 2 had an enantiomer enrichment of 80-86% e.e. (as found by trapping). Hence, 2 has a considerably higher configurational stability than its lithium counterpart 1.

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收藏

页码：633 / 638

页数：6

相关论文

共 43 条

[1] CHIRAL DIAMINES FOR A NEW PROTOCOL TO DETERMINE THE ENANTIOMERIC COMPOSITION OF ALCOHOLS, THIOLS, AND AMINES BY P-31, H-1, C-13, AND F-19 NMR [J].

ALEXAKIS, A ;

FRUTOS, JC ;

MUTTI, S ;

MANGENEY, P .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3326-3334

[2] A NEW REAGENT FOR THE DETERMINATION OF THE OPTICAL PURITY OF PRIMARY, SECONDARY, AND TERTIARY CHIRAL ALCOHOLS AND OF THIOLS [J].

ALEXAKIS, A ;

MUTTI, S ;

MANGENEY, P .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) :1224-1237

[3]

CHAMBERLIN AR, 1984, TETRAHEDRON, V40, P2297

[4] PEROXIDES OF ELEMENTS OTHER THAN CARBON .16. AUTOXIDATION OF EPIMERIC NORBORNYLMAGNESIUM HALIDES [J].

DAVIES, AG ;

ROBERTS, BP .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1969, (03) :317-&

[5] DESIGN AND REACTIVITY OF TOPOLOGICALLY UNIQUE, CHIRAL PHOSPHONAMIDES - REMARKABLE DIASTEREOFACIAL SELECTIVITY IN ASYMMETRIC OLEFINATION AND ALKYLATION [J].

HANESSIAN, S ;

DELORME, D ;

BEAUDOIN, S ;

LEBLANC, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (19) :5754-5756

[6]

HEILMANN R, 1957, B SOC CHIM FR, P119

[7] CHIRAL ORGANOMETALLIC REAGENTS .5. A TEST ON THE CONFIGURATIONAL STABILITY OF CHIRAL ORGANOLITHIUM COMPOUNDS BASED ON KINETIC RESOLUTION - SCOPE AND LIMITATIONS [J].

HIRSCH, R ;

HOFFMANN, RW .

CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (04) :975-982

[8] CHIRAL ORGANOMETALLIC REAGENTS .11. STEREOSELECTIVE EXCHANGE OF DIASTEREOTOPIC IODINE ATOMS BY MAGNESIUM IN 3-ALKOXY-1,1-DIIODOALKANES [J].

HOFFMANN, RW ;

KUSCHE, A .

CHEMISCHE BERICHTE, 1994, 127 (07) :1311-1316

[9] ON THE CONFIGURATIONAL STABILITY OF ALPHA-PHENYLSELENO-ALKYL-LITHIUM COMPOUNDS [J].

HOFFMANN, RW ;

JULIUS, M ;

OLTMANN, K .

TETRAHEDRON LETTERS, 1990, 31 (51) :7419-7422

[10] ESTIMATION OF THE CONFIGURATIONAL STABILITY OF CHIRAL ORGANOMETALLIC REAGENTS [J].

HOFFMANN, RW ;

LANZ, J ;

METTERNICH, R ;

TARARA, G ;

HOPPE, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (11) :1145-1146

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