Development of a polymer bound Wittig reaction and use in multi-step organic synthesis for the overall conversion of alcohols to β-hydroxyamines

被引：62

作者：

Bolli, MH ^{[1
]}

Ley, SV ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 15期

关键词：

D O I：

10.1039/a803612h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient combinatorial access to beta-hydroxyamines suitable for automation is achieved by the mild oxidation of alcohols to aldehydes by polymer supported perruthenate (PSP), the subsequent clean olefination of the obtained aldehydes by polymer supported Wittig reagents followed by the epoxidation of the olefins by dimethyldioxirane (DMDO), and the final aminolysis of the epoxides with various amines is described.

引用

页码：2243 / 2246

页数：4

共 17 条

[1] WITTIG REAGENTS BOUND TO CROSS-LINKED POLYSTYRENES
BERNARD, M
FORD, WT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (03) : 326 - 332
[2] BESTMANN HJ, 1983, TOP CURR CHEM, V109, P85
[3] FORMATION OF Z-1-VINYLIODIDES VIA THE WITTIG REACTION
BESTMANN, HJ
RIPPEL, HC
DOSTALEK, R
[J]. TETRAHEDRON LETTERS, 1989, 30 (39) : 5261 - 5262
[4] CAMPS F, 1971, TETRAHEDRON LETT, P1715
[5] EPOXIDATION OF ALKENES BY DIOXIRANE INTERMEDIATES GENERATED IN THE REACTION OF POTASSIUM CAROATE WITH KETONES
CURCI, R
FIORENTINO, M
TROISI, L
EDWARDS, JO
PATER, RH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) : 4758 - 4760
[6] FORD WT, 1986, ACS SYM SER, V308, P155
[7] Clean three-step synthesis of 4,5-dihydro-1H-pyrazoles starting from alcohols using polymer supported reagents
Haunert, F
Bolli, MH
Hinzen, B
Ley, SV
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (15): : 2235 - 2237
[8] POLYMERIC WITTIG REAGENTS
HEITZ, W
MICHELS, R
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1972, 11 (04) : 298 - &
[9] HEITZ W, 1973, LIEBIGS ANN CHEM, P227
[10] Synthesis of isoxazolidines using polymer supported perruthenate (PSP)
Hinzen, B
Ley, SV
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (01): : 1 - 2

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