A convenient procedure for preparation of 1-(1-aminoalkyl)-1-cyclopropanols from N-benzyl α-amino acid esters

被引：8

作者：

Lysenko, IL ^{[1
]}

Kulinkovich, OG ^{[1
]}

机构：

[1] Byelorussian State Univ, Minsk 220050, BELARUS

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 37卷 / 09期

关键词：

D O I：

10.1023/A:1013158900003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of N-benzyl alpha-amino acid ethyl esters with ethylmagnesium bromide in the presence of a catalytic amount of titanium tetraisopropoxide leads to formation of the corresponding 1-aminoalkyl-1-cyclopropanols in high yields. Hydrogenation of the latter over palladium catalyst ensures selective removal of one or two protecting benzyl groups from the nitrogen atom.

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页码：1238 / 1243

页数：6

相关论文

共 19 条

[1] Enantioselective syntheses of a 1 alpha-hydroxyvitamin D ring A precursor from 3-(triphenylsilyl)glycidol and from malic acid [J].

Achmatowicz, B ;

Jankowski, P ;

Wicha, J .

TETRAHEDRON LETTERS, 1996, 37 (31) :5589-5592

[2] HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF THREO OR ERYTHRO AMINOALKYL EPOXIDES FROM ALPHA-AMINO-ACIDS [J].

BARLUENGA, J ;

BARAGANA, B ;

CONCELLON, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6696-6699

[3] SYNTHESIS AND BIOLOGICAL EVALUATION OF CYCLOPROPYL ANALOGS OF 2-AMINO-5-PHOSPHONOPENTANOIC ACID [J].

DAPPEN, MS ;

PELLICCIARI, R ;

NATALINI, B ;

MONAHAN, JB ;

CHIORRI, C ;

CORDI, AA .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (01) :161-168

[4] ELEVATION OF SERUM CORTICOSTERONE IN RATS BY BREMAZOCINE, A KAPPA-OPIOID AGONIST [J].

FULLER, RW ;

LEANDER, JD .

JOURNAL OF PHARMACY AND PHARMACOLOGY, 1984, 36 (05) :345-346

[5] ESTERS OF N-SUBSTITUTED PIPERIDINE CARBOXYLIC ACIDS [J].

HILL, AJ ;

SHEPARD, RA .

JOURNAL OF ORGANIC CHEMISTRY, 1954, 19 (11) :1802-1806

[6] New synthetic route to the alkaloid withasomnine by ring transformation of a functionalized cyclopropanol via the parent pyrrolo[1,2-b]pyrazole [J].

Kulinkovich, O ;

Masalov, N ;

Tyvorskii, V ;

DeKimpe, N ;

Keppens, M .

TETRAHEDRON LETTERS, 1996, 37 (07) :1095-1096

[7]

KULINKOVICH OG, 1991, ZH ORG KHIM+, V27, P1428

[8]

KULINKOVICH OG, 1989, ZH ORG KHIM+, V25, P2244

[9] TITANIUM(IV) ISOPROPOXIDE-CATALYZED FORMATION OF 1-SUBSTITUTED CYCLOPROPANOLS IN THE REACTION OF ETHYLMAGNESIUM BROMIDE WITH METHYL ALKANECARBOXYLATES [J].

KULINKOVICH, OG ;

SVIRIDOV, SV ;

VASILEVSKI, DA .

SYNTHESIS-STUTTGART, 1991, (03) :234-234

[10] REARRANGEMENTS DURING SYNTHESIS OF SUBSTITUTED 1-BENZYLPYRROLIDINES AND 3-SUBSTITUTED 1-BENZYLPIPERIDINES [J].

MORAGUES, J ;

PRIETO, J ;

SPICKETT, RGW ;

VEGA, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (09) :938-940