REGIOSPECIFIC REDUCTIVE RING-CLEAVAGE OF N-SUBSTITUTED AZIRIDINE-2-CARBOXYLATES AND AN AZIRIDINE-2-METHANOL VIA CATALYTIC-HYDROGENATION USING PD AS A CATALYST

被引：66

作者：

LIM, YH ^{[1
]}

LEE, WK ^{[1
]}

机构：

[1] SOGANG UNIV, DEPT CHEM, SEOUL 121742, SOUTH KOREA

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 46期

关键词：

D O I：

10.1016/0040-4039(95)01814-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regiospecific reductive ring cleavage was accomplished in the reaction of N-alpha-methylbenzyl substituted aziridine-2-carboxylate and aziridine-2-methanol under a catalytic hydrogenation condition, The regiospecificity was determined by the substituent at C-2.

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页码：8431 / 8434

页数：4

相关论文

共 26 条

[1] SYNTHESIS AND ANTITUMOR-ACTIVITY OF NOVEL 6-ALKYL-6-DEMETHYLMITOMYCINS [J].

ARAI, H ;

KANDA, Y ;

ASHIZAWA, T ;

MORIMOTO, M ;

GOMI, K ;

KONO, M ;

KASAI, M .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (12) :1805-1809

[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] NUCLEOPHILIC RING-OPENING OF AZIRIDINE-2-CARBOXYLATES WITH WITTIG REAGENTS - AN ENANTIOEFFICIENT SYNTHESIS OF UNSATURATED AMINO-ACIDS [J].

BALDWIN, JE ;

ADLINGTON, RM ;

ROBINSON, NG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (03) :153-155

[4] AMINO-ACID SYNTHESIS VIA RING-OPENING OF N-SULFONYL AZIRIDINE-2-CARBOXYLATE ESTERS WITH ORGANOMETALLIC REAGENTS [J].

BALDWIN, JE ;

SPIVEY, AC ;

SCHOFIELD, CJ ;

SWEENEY, JB .

TETRAHEDRON, 1993, 49 (28) :6309-6330

[5] THE RING-OPENING OF AZIRIDINE-2-CARBOXYLATE ESTERS WITH ORGANOMETALLIC REAGENTS [J].

BALDWIN, JE ;

ADLINGTON, RM ;

ONEIL, IA ;

SCHOFIELD, C ;

SPIVEY, AC ;

SWEENEY, JB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) :1852-1854

[6] SYNTHESIS OF N-SUBSTITUTED AZIRIDINE-2-CARBOXYLATES [J].

BERNSTEIN, Z ;

BENISHAI, D .

TETRAHEDRON, 1977, 33 (08) :881-883

[7]

BODENAN J, 1992, SYNTHESIS-STUTTGART, P288

[8] SYNTHESIS OF ALPHA-AMINO-ACIDS BY RING-OPENING OF AZIRIDINE-2-CARBOXYLATES WITH CARBON NUCLEOPHILES [J].

CHURCH, NJ ;

YOUNG, DW .

TETRAHEDRON LETTERS, 1995, 36 (01) :151-154

[9] SYNTHESIS OF THE AZIRIDINO[1,2-A]PYRROLIDINE SUBSTRUCTURE OF THE ANTITUMOR AGENTS AZINOMYCIN-A AND AZINOMYCIN-B [J].

COLEMAN, RS ;

CARPENTER, AJ .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :5813-5815

[10] ASYMMETRIC-SYNTHESIS AND REACTIONS OF CIS-N-(P-TOLUENESULFINYL)AZIRIDINE-2-CARBOXYLIC ACIDS [J].

DAVIS, FA ;

ZHOU, P ;

REDDY, GV .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3243-3245