SYNTHESIS OF GAMMA-HYDROXY-ALPHA-AMINO ACIDS BY DIRECTED HYDROXYLATION VIA A DIHYDRO-1,3-OXAZINE INTERMEDIATE

被引：26

作者：

AVENOZA, A

CATIVIELA, C

PEREGRINA, JM

机构：

[1] UNIV ZARAGOZA, CSIC, INST CIENCIA MAT ARAGON, DEPT ORGAN CHEM, E-50009 ZARAGOZA, SPAIN

[2] UNIV LA RIOJA, DEPT CHEM ORGAN CHEM, EDIFICIO CIENTIFICOTECN, SECC CIENCIAS, E-26001 LOGRONO, SPAIN

来源：

TETRAHEDRON | 1994年 / 50卷 / 33期

关键词：

D O I：

10.1016/S0040-4020(01)89617-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The amide group of gamma,delta-unsaturated amino acids can be used for the preparation of gamma hydroxy-alpha-amino acids. Product 2, which is easily obtained by hydrolysis of the spiro-oxazolone-adduct formed in the Diels-Alder reaction between (Z)-2-phenyl-4-benzylidene-5 (4H)-oxazolone 1 and 1,3-butadiene, was converted into the corresponding iodo-1,3-oxazine 3 with I-2/dioxane. Further deiodination and hydrolysis of this product allows the obtention of the free gamma-hydroxy-alpha-amino acid 8.

引用

页码：10021 / 10028

页数：8

共 50 条

[1] ALDEHYDES FROM DIHYDRO-1,3-OXAZINES .4. A NEW SYNTHESIS OF GAMMA-HYDROXY ALDEHYDES AND THEIR GAMMA-OXO DERIVATIVES
ADICKES, HW
POLITZER, IR
MEYERS, AI
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (08) : 2155 - &
[2] THE SYNTHESIS OF A FUNGAL ISONITRILE ANTIBIOTIC VIA A NOVEL RADICAL-ADDITION ELIMINATION-REACTION
BALDWIN, JE
KELLY, DR
ZIEGLER, CB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (02) : 133 - 134
[3] Barrett G.C., 1985, CHEM BIOCH AMINO ACI, P246
[4] 2-OXAZOLINES (4,5-DIHDRO-OXAZOLES) BY ORGANOSELENIUM-INDUCED CYCLIZATION OF ALLYLIC UREAS
BETANCOR, C
LEON, EI
PRANGE, T
SALAZAR, JA
SUAREZ, E
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (08) : 450 - 452
[5] A NEW APPROACH TO (+/-)-2-AMINO-2-DEOXYTETRITOL DERIVATIVES
BONGINI, A
CARDILLO, G
ORENA, M
SANDRI, S
TOMASINI, C
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (05): : 935 - 939
[6] REGIOCONTROLLED AND STEREOCONTROLLED SYNTHESIS OF EPOXY ALCOHOLS AND TRIOLS FROM ALLYLIC AND HOMOALLYLIC ALCOHOLS VIA IODO CARBONATES
BONGINI, A
CARDILLO, G
ORENA, M
PORZI, G
SANDRI, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (24) : 4626 - 4633
[7] IODOCYCLOFUNCTIONALIZATION OF (E)-1-TRICHLOROACETIMIDOALK-2-ENES - SYNTHESIS OF (+/-)-ERYTHRO-SPHINGANINE TRIACETATE
BONGINI, A
CARDILLO, G
ORENA, M
SANDRI, S
TOMASINI, C
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (08): : 1345 - 1349
[8] ENANTIOSPECIFIC SYNTHESIS WITH AMINO-ACIDS .1. TRYPTOPHAN AS A CHIRON FOR THE SYNTHESIS OF ALPHA-SUBSTITUTED TRYPTOPHAN DERIVATIVES
BOURNE, GT
CRICH, D
DAVIES, JW
HORWELL, DC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (07): : 1693 - 1699
[9] CONFORMATIONALLY RESTRICTED AMINO-ACIDS - DIASTEREOSELECTIVE SUBSTITUTION AT THE BETA-POSITION OF L-TRYPTOPHAN
BRUNCKO, M
CRICH, D
[J]. TETRAHEDRON LETTERS, 1992, 33 (42) : 6251 - 6254
[10] BURKERT U, 1982, MOL MECHANICS

← 1 2 3 4 5 →