Stereoselectivity of the reactions of n-phthaloyl iminium ions and amino-substituted radicals derived from threonine

被引：19

作者：

Renaud, P

Stojanovic, A

机构：

[1] Université de Fribourg, Institut de Chimie Organique, Pérolles

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 15期

关键词：

D O I：

10.1016/0040-4039(96)00387-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of phthalimido-substituted radicals of type B and iminium ions of type C have been investigated. Similar stereoselectivities were observed in both cases and explained by a model based on minimization of allylic 1,3-strain. The first intermolecular radical addition to the a beta-substituted dehydroamino acid is reported. Copyright (C) 1996 Published by Elsevier Science Ltd

引用

页码：2569 / 2572

页数：4

共 20 条

[1] DIASTEREOSELECTIVE RADICAL-ADDITION TO METHYLENEOXAZOLIDINONES - AN ENANTIOSELECTIVE ROUTE TO ALPHA-AMINO-ACIDS [J].

AXON, JR ;

BECKWITH, ALJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (05) :549-550

[2] SYNTHESIS OF NOVEL ALPHA-AMINO-ACIDS AND DERIVATIVES USING RADICAL CHEMISTRY - SYNTHESIS OF L-ALPHA-AMINO-ADIPIC AND D-ALPHA-AMINO-ADIPIC ACIDS, L-ALPHA-AMINOPIMELIC ACID AND APPROPRIATE UNSATURATED DERIVATIVES [J].

BARTON, DHR ;

HERVE, Y ;

POTIER, P ;

THIERRY, J .

TETRAHEDRON, 1987, 43 (19) :4297-4308

[3] DIASTEREOSELECTIVE RADICAL-ADDITION TO DERIVATIVES OF DEHYDROALANINE AND OF DEHYDROLACTIC ACID [J].

BECKWITH, ALJ ;

CHAI, CLL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (16) :1087-1088

[4] 1,2-STEREOINDUCTION IN RADICAL REACTIONS - STEREOSELECTIVE SYNTHESIS OF 2-ALKYL-3-HYDROXYBUTANOATES [J].

BULLIARD, M ;

ZEHNDER, M ;

GIESE, B .

HELVETICA CHIMICA ACTA, 1991, 74 (07) :1600-1607

[5] METHYLENE PIPERAZINE-2,5-DIONES AS TEMPLATES FOR THE SYNTHESIS OF AMINO-ACID DERIVATIVES [J].

CHAI, CLL ;

KING, AR .

TETRAHEDRON LETTERS, 1995, 36 (24) :4295-4298

[6] FREE-RADICAL ADDITION TO DIPEPTIDES AND TRIPEPTIDES CONTAINING DEHYDROALANINE RESIDUES [J].

CRICH, D ;

DAVIES, JW .

TETRAHEDRON, 1989, 45 (17) :5641-5654

[7]

Curran D P, 1995, STEREOCHEMISTRY RADI

[8] CRAM RULE FOR RADICALS - STEREOSELECTIVE HYDROGEN ABSTRACTION REACTIONS OF N-H SUBSTITUTED RADICALS [J].

CURRAN, DP ;

SUN, SN .

TETRAHEDRON LETTERS, 1993, 34 (39) :6181-6184

[9] ADDITIONS OF MALONONITRILE RADICALS TO ALKENES - NEW EXAMPLES OF 1,2-ASYMMETRIC INDUCTION IN IODINE AND PHENYLSELENIUM TRANSFER-REACTIONS [J].

CURRAN, DP ;

THOMA, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (11) :4436-4437

[10] GROUP TRANSFER ADDITION-REACTIONS OF METHYL(PHENYLSELENO)MALONONITRILE TO ALKENES [J].

CURRAN, DP ;

EICHENBERGER, E ;

COLLIS, M ;

ROEPEL, MG ;

THOMA, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (10) :4279-4288

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