Substituted epoxides by lithiation of terminal epoxides

被引：18

作者：

Hodgson, DM ^{[1
]}

Reynolds, NJ ^{[1
]}

Coote, SJ ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 23期

关键词：

D O I：

10.1021/ol048544j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diamine-ligand-assisted direct hydrogen-lithium exchange allows the generation of nonstabilized (H-substituted) oxiranyllithium species and their subsequent trapping by Bu3SnCl and carbonyl-based electrophiles. This reaction provides a new concise route to alpha,beta-epoxystannanes and substituted epoxides.

引用

页码：4187 / 4189

页数：3

共 50 条

[41] FRIEDEL CRAFTS CYCLIALKYLATIONS OF SOME EPOXIDES .3. CYCLIZATIONS OF TERTIARY AND META-SUBSTITUTED ARYLALKYL EPOXIDES
TAYLOR, SK
BLANKESPOOR, CL
HARVEY, SM
RICHARDSON, LJ
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14): : 3309 - 3312
[42] LITHIUM DIMETHYLCUPRATE REACTION WITH OXYGEN-SUBSTITUTED EPOXIDES
HARTMAN, BC
LIVINGHO.T
RICKBORN, B
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (25): : 4346 - 4348
[43] COPOLYMERIZATION OF 3,4-DIMETHYLTETRAHYDROFURAN WITH SUBSTITUTED EPOXIDES
MALANGA, M
VOGL, O
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1981, 182 (AUG): : 147 - POLY
[44] CATIONIC AND COORDINATIVE POLYMERIZATION OF FUNCTIONAL EPOXIDES AND SUBSTITUTED TETRAHYDROFURANS
VOGL, O
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1985, 189 (APR-): : 5 - POLY
[45] Mild cleavage of aliphatic epoxides with substituted anilines on alumina
Harrak, Y
Pujol, MD
TETRAHEDRON LETTERS, 2002, 43 (05) : 819 - 822
[46] The effects of conformation and solvation on optical rotation: Substituted epoxides
Wilson, Shaun M.
Wiberg, Kenneth B.
Murphy, Michael J.
Vaccaro, Patrick H.
CHIRALITY, 2008, 20 (3-4) : 357 - 369
[47] ALKALI-METAL O,O-DIETHYL PHOSPHOROTELLUROATES, A REAGENT CLASS FOR DEOXYGENATION OF EPOXIDES, ESPECIALLY TERMINAL EPOXIDES
CLIVE, DLJ
MENCHEN, SM
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (12): : 2347 - 2354
[48] ALPHA, ALPHA-DISUBSTITUTED EPOXIDES WITH ELECTRON ATTRACTING GROUPS .3. SYNTHESIS AND ACTIVITY OF VARIOUSLY SUBSTITUTED EPOXIDES
ROBERT, A
FOUCAUD, A
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1969, (07): : 2537 - &
[49] BASE-PROMOTED REACTIONS OF EPOXIDES .4. FORMATION OF SUBSTITUTED OLEFINS FROM REACTION OF EPOXIDES WITH ORGANOLITHIUM REAGENTS
CRANDALL, JK
LIN, LHC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (17) : 4527 - &
[50] Highly enantioselective resolution of terminal epoxides using polymeric catalysts
Song, YM
Yao, XQ
Chen, HL
Bai, CM
Hu, XQ
Zheng, Z
TETRAHEDRON LETTERS, 2002, 43 (37) : 6625 - 6627

← 1 2 3 4 5 →