gamma-silyloxy-benzyllithiums: Stereochemistry of the retro-[1,4]-Brook rearrangement

被引：12

作者：

Bousbaa, J ^{[1
]}

Ooms, F ^{[1
]}

Krief, A ^{[1
]}

机构：

[1] FAC UNIV NOTRE DAME PAIX,DEPT CHEM,LAB CHIM ORGAN SYNTHESE,B-5000 NAMUR,BELGIUM

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 43期

关键词：

D O I：

10.1016/S0040-4039(97)01810-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Although gamma-sulfonyloxy-benzylselenides react with butyllithium to produce stereospecifically aryl cyclopropanes, the corresponding gamma-silyloxy-benzylselenides lead to a stereoisomeric mixture of gamma-hydroxy-alpha-silyl-benzylselenides via the retro-[1,4]-Brook rearrangement. Apparently the intermediate benzyllithiums are alkylated before epimerisation takes place in the first case, whereas in the second one epimerisation occurs prior to the silyl group migration. (C) 1997 Elsevier Science Ltd.

引用

页码：7625 / 7628

页数：4

共 37 条

[21] STEREOCHEMICAL OUTCOME OF BENZYLLITHIUMS SYNTHESIS FROM SELENIDES [J].

KRIEF, A ;

HOBE, M ;

DUMONT, W ;

BADAOUI, E ;

GUITTET, E ;

EVRARD, G .

TETRAHEDRON LETTERS, 1992, 33 (23) :3381-3384

[22] 1,4-SILYL MIGRATION REACTIONS - APPLICABILITY TO ALKYLPROPYLSILANES, VINYLPROPYLSILANES, AND CYCLOPROPYLSILANES [J].

LAUTENS, M ;

DELANGHE, PHM ;

GOH, JB ;

ZHANG, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3270-3272

[23]

Marshall J. A., 1991, COMPREHENSIVE ORGANI, V3, P975

[24] REGIOCHEMICALLY AND STEREOCHEMICALLY DEFINED SYNTHESIS OF ALLYLSILANES [J].

MARUMOTO, S ;

KUWAJIMA, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (20) :9021-9024

[25]

MARUMOTO S, 1992, J AM CHEM SOC, V114, P1421

[26] REVERSIBLE 1,4 MIGRATION OF A SILYL GROUP FROM OXYGEN TO CARBON - AN UNEXPECTED ROUTE TO ALPHA-TRIALKYLSILYL KETOXIMES [J].

MORA, J ;

COSTA, A .

TETRAHEDRON LETTERS, 1984, 25 (32) :3493-3496

[27]

NOYORI R, 1992, TETRAHEDRON, V33, P6529

[28]

PEDRETTI V, 1987, TETRAHEDRON, V28, P5965

[29] ANIONIC 1,4 O-]C SILYL REARRANGEMENTS [J].

RUCKER, C .

TETRAHEDRON LETTERS, 1984, 25 (39) :4349-4352

[30]

SAMMFLEBEN F, 1997, TETRAHEDRON LETT, V32, P3893

← 1 2 3 4 →