Synthesis of bornene-2,2′-diamino-1,1′-binaphthalene conjugates in palladium-catalysed aminocarbonylations

被引：13

作者：

Mikle, Gabor ^{[1
,2
]}

Boros, Borbala ^{[3
]}

Kollar, Laszlo ^{[1
,2
,4
]}

机构：

[1] Univ Pecs, Dept Inorgan Chem, POB 266, H-7624 Pecs, Hungary

[2] Szentagothai Res Ctr, POB 266, H-7624 Pecs, Hungary

[3] Univ Pecs, Dept Analyt & Environm Chem, Ifjusag U 6, H-7624 Pecs, Hungary

[4] MTA PTE Res Grp Select Chem Synth, Ifjusag U 6, H-7624 Pecs, Hungary

来源：

TETRAHEDRON-ASYMMETRY | 2016年 / 27卷 / 9-10期

基金：

匈牙利科学研究基金会;

关键词：

CARBONYLATION; ARYL; IODOALKENE; RESOLUTION; COMPLEXES; MECHANISM;

D O I：

10.1016/j.tetasy.2016.03.010

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Palladium-catalysed aminocarbonylation of a terpenoic iodoalkene (2-iodo-bornene) model compound with both enantiomerically pure and racemic 2,2'-diamino-1,1'-binaphthalene (BINAM) as the N-nucleophile was carried out. All of the diastereoisomers of the monocarboxamide (N-bornenyl carboxamide) and dicarboxamide (N,N'-dinorbomenylcarboxamide) derivatives were synthesised. The diastereoselectivities of the aminocarbonylation were investigated in both cases: either racemic BINAM was used as the N-nucleophile in the aminocarbonylation of enantiomerically pure 2-iodobornene or racemic iodobornene was aminocarbonylated with enantiomerically pure BINAM with moderate diastereoselectivities. In this way, all possible diastereoisomers of binaphthalene-bornene conjugates were synthesised in moderate to high yields by asymmetric (diastereoselective) aminocarbonylation. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：377 / 383

页数：7

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