Constrained 1-Phenylethyl Amine Analogues as Chiral Auxiliaries in Stereoselective trans-β-Lactam Formation via Staudinger Cycloaddition

被引：2

作者：

Kurteva, Vanya ^{[1
]}

Alexandrova, Maria ^{[1
]}

机构：

[1] Bulgarian Acad Sci, Inst Organ Chem, Ctr Phytochem, Acad G Bonchev St,Bl 9, BU-1113 Sofia, Bulgaria

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2019年 / 56卷 / 03期

关键词：

THIENAMYCIN; MILLENNIUM; CEPHEMS;

D O I：

10.1002/jhet.3471

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The efficiency of enantiomeric 1-aminoindane and 1,2,3,4-tetrahydro-1-naphthylamine as chiral auxiliaries in trans-beta-lactam formation via Staudinger cycloaddition is examined. Aromatic aldehydes possessing one, two, or three methoxyl groups are used as imine precursors, and the influence of their number and position on the reaction output is studied. A comparison with the results obtained from 1-phenylethyl and 1-(2-naphthyl)ethylamine-derived imines is performed.

引用

页码：930 / 937

页数：8

共 5 条

[1] Naphthylethylamines as chiral auxiliaries in a stereoselective formation of trans-β-lactams via Staudinger cycloaddition
Kurteva, Vanya B.
Todorov, Aleksandar R.
Stoylova-Dicheva, Margarita
ARKIVOC, 2011, : 198 - 212
[2] Chiral amine-induced stereoselectivity in trans-β-lactam formation via Staudinger cycloaddition
Todorov, Aleksandar R.
Kurteva, Vanya B.
Bontchev, Ranko P.
Vassilev, Nikolay G.
TETRAHEDRON, 2009, 65 (50) : 10339 - 10347
[3] Microwave-Induced Stereocontrol of β-Lactam Formation with an N-Benzylidene-9,10-dihydrophenanthren-3-amine via Staudinger Cycloaddition
Bandyopadhyay, Debasish
Banik, Bimal K.
HELVETICA CHIMICA ACTA, 2010, 93 (02) : 298 - 301
[4] STEREOSELECTIVE EFFECTS IN REACTIONS OF METAL COMPLEXES .2. SELECTIVITY IN COMPLEX FORMATION OF NICKEL(II)-, COPPER(II)-AND ZINC(II)-(D) PROPYLENEDIAMINETETRAACETATE WITH RACEMIC 1-PHENYLETHYL AMINE
BERNAUER, K
JEANNERE.MF
VONDERSC.D
HELVETICA CHIMICA ACTA, 1971, 54 (01) : 297 - &
[5] Microwave-Induced Enantiospecific Synthesis of trans-(3R,4R)-3-Acetoxy-4-aryl-1-(chrysen-6-yl)azetidin-2-ones via the Staudinger Cycloaddition Reaction of (+)-Car-3-ene with Polyaromatic Imines
A. L. Shaikh
R. N. Yadav
B. K. Banik
Russian Journal of Organic Chemistry, 2020, 56 : 910 - 915

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