Estrone derived 2-naphthol analogue in the diastereoselective one-pot Betti-condensation

被引：5
|
作者：
Zagranyarska, Irena [1 ]
Kostova, Kalina [1 ]
Zagranyarski, Yulian [2 ]
Nikolova, Rositsa [3 ]
Shivachev, Boris [3 ]
Dimitrov, Vladimir [1 ]
机构：
[1] Bulgarian Acad Sci, Inst Organ Chem, Ctr Phytochem, Acad G Bonchev 9, Sofia 1113, Bulgaria
[2] Sofia Univ St Kliment Ohridski, Fac Chem & Pharm, 1 James Bourchier Blvd, Sofia 1164, Bulgaria
[3] Bulgarian Acad Sci, Inst Mineral & Crystallog Acad Ivan Kostov, Acad G Bonchev 107, Sofia 1113, Bulgaria
来源：
MOLECULAR DIVERSITY | 2020年 / 24卷 / 04期
关键词：
Deoxy-isoequilenine; Betti-condensation; Chiral ligands; Absolute configuration; Diethylzinc addition; HIGHLY ENANTIOSELECTIVE ADDITION; ABSOLUTE-CONFIGURATION; EFFICIENT SYNTHESIS; IN-VITRO; DIETHYLZINC; BASE; LIGANDS; DIALKYLZINCS; DERIVATIVES; CATALYSTS;
D O I：
10.1007/s11030-019-09998-5
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The utility of deoxy-isoequilenine synthesized from estrone as valuable 2-naphthol analogue is demonstrated in the three components Betti-condensation. A simple, efficient and green procedure for the synthesis of aminobenzylnaphthol analogues (so-called Betti bases) has been realized highly diastereoselectively by using (S)-phenylethylamine and 1- or 2-naphthaldehyde. The absolute configuration of the new chiral compounds obtained has been determined by means of NMR experiments and confirmed by X-ray crystallography. The chiral steroidal aminobenzylnaphthols have been evaluated as pre-catalysts for the addition of diethylzinc to aldehydes with enantioselectivities of up to 98% ee.
引用
收藏
页码：1343 / 1353
页数：11
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