Novel approach to the synthesis of alpha-alkoxycarbonyl alpha-aminophosphonic esters based on a facile transformation of phosphoranes to phosphonic esters

被引：11

作者：

Seki, M ^{[1
]}

Kondo, K ^{[1
]}

Iwasaki, T ^{[1
]}

机构：

[1] TANABE SEIYAKU CO LTD,APPL BIOCHEM RES LAB,YOKOGAWA KU,OSAKA 532,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 01期

关键词：

D O I：

10.1039/p19960000003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Triethoxyphosphoranes 2, generated in situ from oxamates 1, reacted with bromotrimethylsilane to give alpha-aminophosphonic esters 3 which, in the case of example 13, have been used in a new synthesis of 1-beta-methylcarbapenem 14.

引用

页码：3 / 5

页数：3

共 39 条

[1] NEW SYNTHESIS OF PENEMS, THE OXALIMIDE CYCLIZATION REACTION [J].

AFONSO, A ;

HON, F ;

WEINSTEIN, J ;

GANGULY, AK ;

MCPHAIL, AT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (22) :6138-6139

[2] STEREOSELECTIVE SYNTHESIS OF A 1-AZABICYCLO[3.1.0]HEX-2-YLIDENE DEHYDROAMINO ACID-DERIVATIVE RELATED TO THE AZINOMYCIN ANTITUMOR ANTIBIOTICS [J].

ARMSTRONG, RW ;

MORAN, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (01) :371-372

[3] STEREOSELECTIVE SYNTHESIS OF (E) AND (Z)-1-AZABICYCLO[3.1.0]HEX-2-YLIDENE DEHYDROAMINO ACID-DERIVATIVES [J].

ARMSTRONG, RW ;

TELLEW, JE ;

MORAN, EJ .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2208-2211

[4]

BASHANG G, 1969, HELV CHIM ACTA, V52, P300

[5] SYNTHESIS OF 7-OXO-3-SULPHINYL-1-AZABICYCLO[3.2.0]HEPT-2-ENE-2-CARBOXYLATES - OLIVANIC ACID ANALOGS [J].

BATESON, JH ;

ROBERTS, PM ;

SMALE, TC ;

SOUTHGATE, R .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (04) :185-186

[6] A NEW ROUTE TO PENEMS AND CARBAPENEMS [J].

BATTISTINI, C ;

SCARAFILE, C ;

FOGLIO, M ;

FRANCESCHI, G .

TETRAHEDRON LETTERS, 1984, 25 (22) :2395-2398

[7] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].

BLANCHETTE, MA ;

CHOY, W ;

DAVIS, JT ;

ESSENFELD, AP ;

MASAMUNE, S ;

ROUSH, WR ;

SAKAI, T .

TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186

[8]

COREY EJ, 1967, TETRAHEDRON LETT, P3201

[9] OPTICALLY-ACTIVE 1-AMINOALKYLPHOSPHONIC ACIDS [J].

DHAWAN, B ;

REDMORE, D .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 32 (3-4) :119-144

[10]

FLOYD AJ, 1970, TETRAHEDRON LETT, P1735

← 1 2 3 4 →