1,3-AMINOALCOHOLS BY REDUCTIVE CLEAVAGE OF ISOXAZOLIDINES WITH MOLYBDENUM HEXACARBONYL

被引：224

作者：

CICCHI, S

GOTI, A

BRANDI, A

GUARNA, A

DESARLO, F

机构：

[1] DIPARTIMENTO CHIM ORGAN,VIA G CAPPONI 9,I-50121 FLORENCE,ITALY

[2] UNIV BASILICATA,DIPARTIMENTO CHIM,I-85100 POTENZA,ITALY

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 23期

关键词：

D O I：

10.1016/S0040-4039(00)89062-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Isoxazolidines are reductively cleaved to 1,3-aminoalcohols by reacting with Mo(CO)6 and water. Reaction conditions are simple, mild and selective giving good yields of highly functionalized products with complete retention of configuration of the stereocenters. The reduction fails when steric hindrance is experienced by the nitrogen atom. © 1990.

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页码：3351 / 3354

页数：4

相关论文

共 28 条

[1] SYNTHESIS OF D-BIOTIN FROM L-CYSTINE VIA INTRAMOLECULAR [3+2] CYCLOADDITION [J].

BAGGIOLINI, EG ;

LEE, HL ;

PIZZOLATO, G ;

USKOKOVIC, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (23) :6460-6462

[2] COPE REARRANGEMENT AND INTERNAL CYCLOADDITION OF "5-ALLYL-3,3,5-TRIMETHYL-1-PYRROLINE 1-OXIDE [J].

BAPAT, JB ;

BROWN, RFC ;

BLACK, DSC ;

ICHLOV, C .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1972, 25 (11) :2445-&

[3]

BARALDI PG, 1987, SYNTHESIS-STUTTGART, P276

[4] REACTION OF TRANSITION-METAL CARBONYL WITH HETEROCYCLIC-SYSTEMS .4. REACTION OF FE2(CO)9 WITH 3-PHENYL-2-OXA-3-AZA-[2.2.2]OCT-5-ENE [J].

BECKER, Y ;

EISENSTADT, A ;

SHVO, Y .

TETRAHEDRON, 1978, 34 (06) :799-806

[5]

BREUER E, 1982, CHEM AMINO NITROSE N

[6] 1,3-DIPOLAR ADDITION OF OXIMES TO OLEFINS - CONVERSION OF ALDOXIMES TO NITRILES UNDER MILD CONDITIONS [J].

DALGARD, NKA ;

LARSEN, KE ;

TORSSELL, KBG .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1984, 38 (05) :423-432

[7] STEREOSPECIFIC SYNTHESIS OF RACEMIC DAUNOSAMINE - DIASTEREOFACIAL SELECTIVITY IN A NITRONE CYCLOADDITION [J].

DESHONG, P ;

LEGINUS, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (06) :1686-1688

[8]

DESIMONI G, 1983, ACS MONOGRAPH, V180

[9] NEW SYNTHESIS OF AZEPIN-4-ONES BY FLASH VACUUM THERMOLYSIS OF DIHYDRO AND TETRAHYDROISOXAZOLE-5-SPIROCYCLOBUTANE DERIVATIVES [J].

GOTI, A ;

BRANDI, A ;

DESARLO, F ;

GUARNA, A .

TETRAHEDRON LETTERS, 1986, 27 (43) :5271-5274

[10]

GUARNA A, 1989, SYNTHESIS-STUTTGART, P175