Novel (+)-3-Carene Derivatives and Their Application in Asymmetric Synthesis

被引：4
作者：
Roszkowski, Piotr [1 ]
Malecki, Pawel [1 ]
Maurin, Jan K. [2 ,3 ]
Czarnocki, Zbigniew [1 ]
机构：
[1] Univ Warsaw, Fac Chem, PL-02093 Warsaw, Poland
[2] Natl Med Inst, PL-00725 Warsaw, Poland
[3] Natl Ctr Nucl Res, PL-05400 Otwock, Poland
来源：
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 04期
关键词：
asymmetric catalysis; chiral auxiliaries; hydrogen transfer; ligands; natural products; ENANTIOSELECTIVE ADDITION; STEREOSELECTIVE-SYNTHESIS; TRANSFER HYDROGENATION; CHIRAL LIGANDS; DIETHYLZINC; (R)-(+)-LIMONENE; CATALYSIS; LIMONENE; KETONES;
D O I：
10.1055/s-0034-1378942
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple synthetic procedure for the preparation of mono-N-tosylated-1,2-diamines derived from (+)-3-carene is described. (+)-3-Carene is transformed into the corresponding N-tosylaziridine derivative using chloramine-T trihydrate. Subsequent ring opening with sodium azide followed by reduction of the azide function gives the optically pure mono-N-tosylated-1,2-diamine. This ligand is effective in asymmetric transfer hydrogenations of aromatic ketones. It can also be transformed into other chiral ligands by alkylation of the amino group for application in the addition of diethylzinc to benzaldehydes.
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页码：569 / 574
页数：6
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