DIETHYL (N-METHOXY-N-METHYLCARBAMOYLMETHYL)PHOSPHONATE - A USEFUL EMMONS-HORNER-WITTIG REAGENT

被引：30

作者：

NETZ, DF ^{[1
]}

SEIDEL, JL ^{[1
]}

机构：

[1] UNIV WISCONSIN,DEPT CHEM,OSHKOSH,WI 54901

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 15期

关键词：

D O I：

10.1016/0040-4039(92)88112-I

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate (1) is easily prepared by heating 2-chloro-N-methoxy-N-methylethanamide and triethylphosphite. Reagent 1 is useful for converting aldehydes and ketones into compounds containing an alpha,beta-unsaturated N-methoxy-N-methylamide group with high E selectivity.

引用

页码：1957 / 1958

页数：2

共 4 条

[1] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS
BLANCHETTE, MA
CHOY, W
DAVIS, JT
ESSENFELD, AP
MASAMUNE, S
ROUSH, WR
SAKAI, T
[J]. TETRAHEDRON LETTERS, 1984, 25 (21) : 2183 - 2186
[2] TOTAL SYNTHESIS OF THE MACROLIDE ANTIBIOTIC CYTOVARICIN
EVANS, DA
KALDOR, SW
JONES, TK
CLARDY, J
STOUT, TJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) : 7001 - 7031
[3] THE WITTIG OLEFINATION REACTION AND MODIFICATIONS INVOLVING PHOSPHORYL-STABILIZED CARBANIONS - STEREOCHEMISTRY, MECHANISM, AND SELECTED SYNTHETIC ASPECTS
MARYANOFF, BE
REITZ, AB
[J]. CHEMICAL REVIEWS, 1989, 89 (04) : 863 - 927
[4] N-METHOXY-N-METHYLAMIDES AS EFFECTIVE ACYLATING AGENTS
NAHM, S
WEINREB, SM
[J]. TETRAHEDRON LETTERS, 1981, 22 (39) : 3815 - 3818

← 1 →