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

共 32 条

[1] ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-BETA-HYDROXY ACIDS USING A CHIRAL PYRIDOXAL-LIKE PYRIDINOPHANE-ZINC COMPLEX AS AN ENZYME MIMIC - SCOPE AND LIMITATION
ANDO, M
WATANABE, J
KUZUHARA, H
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (01) : 88 - 90
[2] CATALYTIC ASYMMETRIC-SYNTHESIS OF CYCLOPROPANE-CARBOXYLIC ACIDS - AN APPLICATION OF CHIRAL COPPER CARBENOID REACTION
ARATANI, T
[J]. PURE AND APPLIED CHEMISTRY, 1985, 57 (12) : 1839 - 1844
[3] GENERAL-METHOD OF DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF BETA-HYDROXY-ALPHA-AMINO ACIDS BY CONDENSATION OF ALDEHYDES AND KETONES WITH GLYCINE
BELOKON, YN
BULYCHEV, AG
VITT, SV
STRUCHKOV, YT
BATSANOV, AS
TIMOFEEVA, TV
TSYRYAPKIN, VA
RYZHOV, MG
LYSOVA, LA
BAKHMUTOV, VI
BELIKOV, VM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (14) : 4252 - 4259
[4] STEREOSPECIFIC CONVERSION OF N,N-DIMETHYLAMPHETAMINE INTO N-METHYL-PSEUDOEPHEDRINE
BLAGG, J
DAVIES, SG
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (10) : 653 - 654
[5] THE CHIRAL POOL AS A SOURCE OF ENANTIOSELECTIVE CATALYSTS AND AUXILIARIES
BLASER, HU
[J]. CHEMICAL REVIEWS, 1992, 92 (05) : 935 - 952
[6] UNE NOUVELLE SYNTHESE DE LOXYTOCINE
BOISSONNAS, RA
GUTTMANN, S
JAQUENOUD, PA
WALLER, JP
[J]. HELVETICA CHIMICA ACTA, 1955, 38 (06) : 1491 - 1507
[7] HIGHLY ENANTIOSELECTIVE, CATALYTIC EPOXIDATION OF TRISUBSTITUTED OLEFINS
BRANDES, BD
JACOBSEN, EN
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16) : 4378 - 4380
[8] SELECTIVE REACTIONS BETWEEN PHENOLS AND FORMALDEHYDE - A NOVEL ROUTE TO SALICYLALDEHYDES
CASIRAGHI, G
CASNATI, G
PUGLIA, G
SARTORI, G
TERENGHI, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (09): : 1862 - 1865
[9] ASYMMETRIC OXIDATION OF SULFIDES TO SULFOXIDES CATALYZED BY TITANIUM COMPLEXES OF N-SALICYLIDENE-L-AMINO ACIDS
COLONNA, S
MANFREDI, A
SPADONI, M
CASELLA, L
GULLOTTI, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (01): : 71 - 73
[10] SYNTHESIS OF CHEMICALLY MODIFIED CYCLODEXTRINS
CROFT, AP
BARTSCH, RA
[J]. TETRAHEDRON, 1983, 39 (09) : 1417 - 1474

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