First direct deprotonation-electrophile trapping of simple epoxides:: Synthesis of α,β-epoxysilanes from terminal epoxides

被引：43

作者：

Hodgson, DM ^{[1
]}

Norsikian, SLM ^{[1
]}

机构：

[1] Univ Oxford, Dyson Perrins Lab, Dept Chem, Oxford OX1 3QY, England

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 03期

关键词：

D O I：

10.1021/ol006948f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The presence of a suitable diamine ligand is the key to achieving ring lithiation-substitution of epoxides without the need for activating substituents on the epoxide and constitutes a new synthetic entry to trans-alpha,beta -epoxysilanes.

引用

页码：461 / 463

页数：3

共 40 条

[1] Deprotonation-electrophile trapping of terminal epoxides
Hodgson, DM
Kirton, EHM
Miles, SM
Norsikian, SLM
Reynolds, NJ
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ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (10) : 1893 - 1904
[2] Enantioselective synthesis of epoxides by α-deprotonation -: electrophile trapping of achiral epoxides
Hodgson, DM
Buxton, TJ
Cameron, ID
Gras, E
Kirton, EHM
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (23) : 4293 - 4301
[3] Straightforward synthesis of α,β-epoxysilanes from terminal epoxides by lithium 2,2,6,6-tetramethylpiperidide-mediated deprotonation-in situ silylation
Hodgson, DM
Reynolds, NJ
Coote, SJ
TETRAHEDRON LETTERS, 2002, 43 (44) : 7895 - 7897
[4] DIRECT REGIOSPECIFIC SYNTHESIS OF BROMOKETONES FROM EPOXIDES
CALO, V
LOPEZ, L
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SYNTHESIS-STUTTGART, 1978, (02): : 139 - 140
[5] Alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine
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[6] Direct catalytic synthesis of enantiopure 5-substituted oxazolidinones from racemic terminal epoxides
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ORGANIC LETTERS, 2005, 7 (10) : 1983 - 1985
[7] A facile and efficient method for synthesis of β-iodocarboxylates from terminal epoxides
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Wei, Bo-Le
Wang, Wen-Qiong
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TETRAHEDRON LETTERS, 2019, 60 (50)
[8] Stereocontrolled Synthesis of trans-Cyclopropyl Sulfones from Terminal Epoxides
Bray, Christopher D.
de Faveri, Giorgio
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (13): : 4652 - 4655
[9] SILICA GEL-CATALYZED ADDITION OF THIOPHENOL TO ALPHA-BETA-EPOXYSILANES AND EPOXIDES - SYNTHESIS OF ALPHA-HYDROXYALDEHYDE DERIVATES FROM ALPHA-BETA-EPOXYSILANES
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POLISH JOURNAL OF CHEMISTRY, 1995, 69 (01) : 78 - 84
[10] DIRECT SYNTHESIS OF SPIRO DELTA-LACTONES FROM CONJUGATED DIENES AND EPOXIDES
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