A NOVEL HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF CYANO ETHERS BY REGIOSELECTIVE RING-OPENING OF CHIRAL OXAZOLIDINIUM METHIODIDES WITH SODIUM-CYANIDE

被引：12

作者：

ANDRES, C ^{[1
]}

DELGADO, M ^{[1
]}

PEDROSA, R ^{[1
]}

RODRIGUEZ, R ^{[1
]}

机构：

[1] UNIV VALLADOLID,FAC CIENCIAS,DEPT QUIM ORGAN,E-47011 VALLADOLID,SPAIN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 51期

关键词：

CHIRAL OXAZOLIDINIUM IODIDES; ALPHA-CYANO ETHERS; DIASTEREOSELECTIVE RING OPENING; ALPHA-HYDROXY ACIDS; ASYMMETRIC SYNTHESIS;

D O I：

10.1016/S0040-4039(00)61422-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sodium cyanide reacts with chiral Oxazolidinium methiodides, prepared by quaternization of oxazolidines with methyl iodide, leading regio- and stereoselectively (de. 82-94%) to cyano ethers in moderate to good chemical yields (51-95%). The open compounds are isolated as a pure diastereomer by a single recrystallization of their ammonium methiodides, and converted into enantiomerically pure alpha-hydroxy acids by heting with a concentrated solution of hydrochloric acid.

引用

页码：8325 / 8328

页数：4

共 18 条

[1]

ALBEROLA A, 1990, SYNTHESIS-STUTTGART, P153

[2] REDUCTIVE RING-OPENING OF EPHEDRINE AND PSEUDOEPHEDRINE-DERIVED OXAZOLIDINIUM METHIODIDES BY SODIUM-BOROHYDRIDE - A DIRECT ACCESS TO NEW CHIRAL AMINE-BORANE ADDUCTS [J].

ANDRES, C ;

DELGADO, M ;

PEDROSA, R .

SYNTHETIC COMMUNICATIONS, 1992, 22 (06) :829-839

[3] A NEW CHIRAL GLYCINE SYNTHON - SYNTHESIS, X-RAY STRUCTURE OF (-)BULLET(2S,4R)-2-ETHOXYCARBONYL-4-PHENYL-1,3-OXAZOLIDINE AND DIASTEREOSELECTIVE NUCLEOPHILIC RING-OPENING TO (R)-ETHYL ALPHA-AMINO CARBOXYLATES [J].

ANDRES, C ;

GONZALEZ, A ;

PEDROSA, R ;

PEREZENCABO, A ;

GARCIAGRANDA, S ;

SALVADO, MA ;

GOMEZBELTRAN, F .

TETRAHEDRON LETTERS, 1992, 33 (33) :4743-4746

[4]

ANDRES C, 1992, SYNLETT, P45

[5] STEREOSELECTIVE RING-OPENING OF CHIRAL OXAZOLIDINES BY REFORMATSKY REAGENTS - AN ENANTIOSELECTIVE ENTRY TO BETA-AMINO ESTERS [J].

ANDRES, C ;

GONZALEZ, A ;

PEDROSA, R ;

PEREZENCABO, A .

TETRAHEDRON LETTERS, 1992, 33 (20) :2895-2898

[6] HIGHLY STEREOSELECTIVE SYNTHESES INVOLVING N-ALKYL-4,4,7-ALPHA-TRIMETHYL-TRANS-OCTAHYDRO-1,3-BENZOXAZINE INTERMEDIATES .2. [J].

ELIEL, EL ;

HE, XC .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2114-2119

[7] STEREOSELECTIVE RADICAL-MEDIATED CYCLIZATION OF NOREPHEDRINE DERIVED ALPHA-IODOAMIDES - EXPERIMENTS AND TS-MODELING [J].

GENNARI, C ;

POLI, G ;

SCOLASTICO, C ;

VASSALLO, M .

TETRAHEDRON-ASYMMETRY, 1991, 2 (08) :793-796

[8] DIASTEREOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO CHIRAL IMINES AND 1,3-OXAZOLIDINES [J].

HIGASHIYAMA, K ;

INOUE, H ;

TAKAHASHI, H .

TETRAHEDRON LETTERS, 1992, 33 (02) :235-238

[9] 3-ARYLSULFONYLOXAZOLIDINES AS CHIRAL TEMPLATES - ASYMMETRIC-SYNTHESIS OF 2-SUBSTITUTED 2-HYDROXYCYCLOHEXANECARBALDEHYDES FROM 2-HYDROXYMETHYLENECYCLOHEXANONE [J].

HOPPE, I ;

HOPPE, D ;

WOLFF, C ;

EGERT, E ;

HERBST, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (01) :67-69

[10] SYNTHESE VON DEPSIPEPTIDEN [J].

LOSSE, G ;

BACHMANN, G .

CHEMISCHE BERICHTE-RECUEIL, 1964, 97 (09) :2671-&

← 1 2 →