Regioselective ring opening of amino epoxides with nitriles:: An easy synthesis of (2R,3S)- and (2S,3S)-1,3-diaminoalkan-2-ols with differently protected amine functions

被引：24

作者：

Concellón, JM ^{[1
]}

Suárez, JR ^{[1
]}

del Solar, V ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 18期

关键词：

D O I：

10.1021/jo051109y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Transformation of enantiopure (2R,1'S)- or (2S,1'S)-2-(laminoalkyl)epoxides 1 or 2 into the corresponding (2R,3S)and (2S,3S)-1,3-diaminoalkan-2-ols 3 or 4 is described. The opening of the epoxide ring with different nitriles (Ritter reaction) takes place with total selectivity and in high yields in the presence of BF(3)center dot Et2O. Interestingly, the two amine groups are differently protected. A mechanism to explain this transformation is proposed.

引用

页码：7447 / 7450

页数：4

共 22 条

[1] 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

[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] Practical, stereoselective synthesis of palinavir, a potent HIV protease inhibitor [J].

Beaulieu, PL ;

Lavallee, P ;

Abraham, A ;

Anderson, PC ;

Boucher, C ;

Bousquet, Y ;

Duceppe, JS ;

Gillard, J ;

Gorys, V ;

GrandMaitre, C ;

Grenier, L ;

Guindon, Y ;

Guse, I ;

Plamondon, L ;

Soucy, F ;

Valois, S ;

Wernic, D ;

Yoakim, C .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (11) :3440-3448

[4] Preparation of aminoalkyl chlorohydrin hydrochlorides: Key building blocks for hydroxyethylamine-based HIV protease inhibitors [J].

Beaulieu, PL ;

Wernic, D .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3635-3645

[5]

Bishop R, 1991, COMPREHENSIVE ORGANI, P261

[6] Ritter-type reactions of N-chlorosaccharin:: A method for the electrophilic diamination of alkenes [J].

Booker-Milburn, KI ;

Guly, DJ ;

Cox, B ;

Procopiou, PA .

ORGANIC LETTERS, 2003, 5 (18) :3313-3315

[7] APPLICATIONS OF RITTER REACTION IN STEROID SERIES .1. PREPARATION OF TRANS ACETAMINO ALCOHOLS FROM 5,6-EPOXIDES - CONFORMATION OF AMIDE GROUP [J].

BOURGERY, G ;

FRANKEL, JJ ;

RYANS, RJ ;

JULIA, S .

TETRAHEDRON, 1972, 28 (06) :1377-+

[8]

Cannarsa MJ, 1996, CHEM IND-LONDON, P374

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

Concellón, JM ;

Suárez, JR ;

García-Granda, S ;

Díaz, MR .

ORGANIC LETTERS, 2005, 7 (02) :247-250

[10] Synthesis of enantiopure imidazolines through a ritter reaction of 2-(1-aminoalkyl)aziridines with nitriles [J].

Concellón, JM ;

Riego, E ;

Suárez, JR ;

García-Granda, S ;

Díaz, MR .

ORGANIC LETTERS, 2004, 6 (24) :4499-4501

← 1 2 3 →