Axially chiral bis(α-amino acid)s and dioxopiperazines.: Synthesis and configurational assignment

被引：12

作者：

Ridvan, L ^{[1
]}

Budesínsky, M ^{[1
]}

Tichy, M ^{[1
]}

Malon, P ^{[1
]}

Závada, J ^{[1
]}

Podlaha, J ^{[1
]}

Císarová, I ^{[1
]}

机构：

[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, Prague 16610, Czech Republic

来源：

TETRAHEDRON | 1999年 / 55卷 / 42期

关键词：

biaryls; amino acids and derivatives; NMR; X-ray crystal structures;

D O I：

10.1016/S0040-4020(99)00717-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conversion of the easily accessible racemic bis(amino acid)s cis- and trans-2a into the Q-enantiomers via the corresponding Schiff bases with (1S,2S,5S)-2-hydroxy-3-pinanone is described. Condensation of the N-Boc-protected bis(amino acid)s with esters of the corresponding axially chiral amino acids (R)- and (S)-1b afforded tetraspiro-substituted bis(dioxopiperazine)s 7 representing a rare case of primary helical topology. Absolute configuration of the products was assigned by NMR and CD spectra and confirmed by X-ray analysis of the Schiff base (S)-cis-3. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：12331 / 12348

页数：18

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