Stereoselective addition of phenyl selenyl chloride to methoxy alkenes derived from N-protected chiral α-amino acids.

被引：13

作者：

Demarcus, M

Filigheddu, SN

Mann, A

Taddei, M

机构：

[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy

[2] Fac Pharm, CNRS, ERS 655, F-67401 Illkirch Graffenstaden, France

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 23期

关键词：

selenium halogen compounds; selenonium ions; chelation; acetals;

D O I：

10.1016/S0040-4039(99)00761-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(E)-Methoxy alkenes derived from N-Boc or NCbz alpha-amino acids undergo stereoselective addition of phenyl selenyl chloride in the presence of Ti(Oi-Pr)(4) and LiCl to give the corresponding phenylselenyl aldehydes that can be easily transformed into new enantiomericalIy pure amino acids containing an aziridine ring. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4417 / 4420

页数：4

共 7 条

[1]

[Anonymous], ANN REP MED CHEM

[2] Small ring constrained peptidomimetics.: Synthesis of aziridine parallel β-sheet mimetics [J].

Filigheddu, SN ;

Taddei, M .

TETRAHEDRON LETTERS, 1998, 39 (22) :3857-3860

[3] Synthesis of 3-aminopyrrolidin-2-ones by an intramolecular reaction of aziridinecarboxamides. [J].

Funaki, I ;

Thijs, L ;

Zwanenburg, B .

TETRAHEDRON, 1996, 52 (29) :9909-9924

[4] A general synthesis of oligopeptides containing an oxirane ring in the place of a peptidic bond [J].

Mann, A ;

Quaranta, L ;

Reginato, G ;

Taddei, M .

TETRAHEDRON LETTERS, 1996, 37 (15) :2651-2654

[5] 1ST ASYMMETRIC-SYNTHESIS OF ENANTIOPURE ALPHA-SULFENYL DITHIOACETALS AND ALPHA-SULFENYL ALDEHYDES [J].

POLI, G ;

BELVISI, L ;

MANZONI, L ;

SCOLASTICO, C .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11) :3165-3168

[6] New peptidic cysteine protease inhibitors derived from the electrophilic α-amino acid aziridine-2,3-dicarboxylic acid [J].

Schirmeister, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (04) :560-572

[7] Chiral aziridinyl radicals: An application to the synthesis of the core nucleus of FR-900482 [J].

Ziegler, FE ;

Belema, M .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) :1083-1094

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