SYNTHESIS, RESOLUTION AND ABSOLUTE-CONFIGURATION DETERMINATION OF (S)-4-FORMYL-5-HYDROXY[2.2]PARACYCLOPHANE AND (R)-4-FORMYL-5-HYDROXY[2.2]PARACYCLOPHANE AND ITS APPLICATION IN THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS

被引：71

作者：

ANTONOV, DY ^{[1
]}

BELOKON, YN ^{[1
]}

IKONNIKOV, NS ^{[1
]}

ORLOVA, SA ^{[1
]}

PISAREVSKY, AP ^{[1
]}

RAEVSKI, NI ^{[1
]}

ROZENBERG, VI ^{[1
]}

SERGEEVA, EV ^{[1
]}

STRUCHKOV, YT ^{[1
]}

TARAROV, VI ^{[1
]}

VORONTSOV, EV ^{[1
]}

机构：

[1] RUSSIAN ACAD SCI,AN NESMEYANOV ORGANOELEMENT CPDS INST,MOSCOW,RUSSIA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 14期

关键词：

D O I：

10.1039/p19950001873

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Racemic (R, S)-4-formyl-5-hydroxy[2.2]paracyclophane (FHPC) was resolved into enantiomers via its Schiff's base with (S)- and (R)-alpha-phenylethylamine (alpha-PEAM) and its absolute configuration was determined by an X-ray diffraction structural study. Scalemic FHPC or its derivatives can be used as chiral auxiliaries for the asymmetric synthesis of beta-hydroxy-alpha-amino acids and alpha-methylphenylalanine with ees ranging mostly from 45 to 98%.

引用

页码：1873 / 1879

页数：7

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