Addition reaction of O-toluamides with chiral auxiliary derived from 2-amino-1,3-propanediols to imines

被引：5

作者：

Chrzanowska, Maria ^{[1
]}

Dreas, Agnieszka ^{[1
]}

机构：

[1] Adam Mickiewicz Univ Poznan, Fac Chem, PL-60780 Poznan, Poland

来源：

HETEROCYCLES | 2006年 / 69卷 / 01期

关键词：

lateral lithiation; asymmetric synthesis; 2-amino-1,3-propanediol; 8-oxoberbine; Pomeranz-Fritsch-Bobbitt synthesis; ASYMMETRIC-SYNTHESIS; PROTOBERBERINE ALKALOIDS; BENZONITRILE CYCLOADDITION; ENANTIOSELECTIVE SYNTHESIS; TERTIARY BENZAMIDES; SHORT ROUTE; CONDENSATION; (S)-(-)-O-METHYLBHARATAMINE; (R)-(+)-O-METHYLBHARATAMINE; PHYLLODULCIN;

D O I：

10.3987/COM-06-S(O)34

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselectivity of the addition reaction of o-toluamides, incorporating 2-amino-1,3-propanediols as chiral auxiliary to imines has been studied. Addition products, diastercomerically enriched, after column chromatography separation were obtained and further transformed to (S)-(-)-or (R)-(+)-8-oxoberbines with ee up to 97%.

引用

页码：303 / +

页数：9

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