Totally selective ring-opening of amino epoxides with ketones:: A general entry to enantiopure (2R,3S)- and (2S,3S)-3-aminoalkano-1,2-diols

被引：19

作者：

Concellón, JM

Suárez, JR

García-Granda, S

Díaz, MR

机构：

[1] Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain

[2] Univ Oviedo, Fac Quim, Dept Quim Fis & Analit, E-33071 Oviedo, Spain

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 02期

关键词：

D O I：

10.1021/ol047785o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Transformation of enantiopure diastereoisomers (2R,1'S)- and (2S,1'S)-2-(1-aminoalkyl)epoxides into the corresponding 4-(1-aminoalkyl)-1,3-dioxolanes is achieved by reaction with different ketones in the presence of (BF3Et2O)-Et-.. The conversion takes place in very high yields. total selectivity, and without epimerization. A mechanism to explain this transformation is proposed. The obtained 1.3-dioxolanes can be deprotected. and (2R,3S)- and (2S,3S)-3-aminoalkano-1,2-diols were isolated.

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页码：247 / 250

页数：4

相关论文

共 16 条

[1] Synthesis of 1,3-dioxolanes by the addition of ketones to epoxides by using [Cp*Ir(NCMe)3]2+ as catalyst [J].

Adams, RD ;

Barnard, TS ;

Brosius, K .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 582 (02) :358-361

[2] THE FIRST DIRECT PREPARATION OF CHIRAL FUNCTIONALIZED KETONES AND THEIR SYNTHETIC USES [J].

BARLUENGA, J ;

BARAGANA, B ;

ALONSO, A ;

CONCELLON, JM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (08) :969-970

[3] 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

[4]

BOGERT MT, 1933, J AM CHEM SOC, V55, P3741

[5]

BUSCI I, 2001, J MOL CATAL, V168, P47

[6] ENANTIOSELECTIVE SYNTHESES USING CHIRAL EPOXY-ALCOHOLS [J].

COLVIN, EW ;

ROBERTSON, AD ;

WAKHARKAR, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (06) :312-314

[7] 2,4,4,6-tetrabromo-2,5-cyclohexadienone (TABCO) as a versatile, efficient, and chemoselective catalyst for the acetalization and transacetalization of carbonyl compounds, the preparation of acetonides from epoxides and acylals (1,1-diacetates) from aldehydes [J].

Firouzabadi, H ;

Iranpoor, N ;

Shaterian, HR .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2002, 75 (10) :2195-2205

[8]

HABIBI M, 1975, CATAL LETT, V3, P205

[9] Efficient and catalytic conversion of epoxides to 1,3-dioxolanes with TiO(TFA)2 or TiCl3(OTf) [J].

Iranpoor, N ;

Zeynizadeh, B .

JOURNAL OF CHEMICAL RESEARCH-S, 1998, (08) :466-467

[10] Ru(III) catalyses the conversion of epoxides to 1,3-dioxolanes. [J].

Iranpoor, N ;

Kazemi, F .

SYNTHETIC COMMUNICATIONS, 1998, 28 (17) :3189-3193