ASYMMETRIC-SYNTHESIS OF CHIRAL CYCLIC AMINO-ACIDS BY DIELS-ALDER REACTIONS OF (2S)-4-METHYLENEOXAZOLIDIN-5-ONES AND (2R)-4-METHYLENEOXAZOLIDIN-5-ONES

被引：38

作者：

PYNE, SG ^{[1
]}

DIKIC, B ^{[1
]}

GORDON, PA ^{[1
]}

SKELTON, BW ^{[1
]}

WHITE, AH ^{[1
]}

机构：

[1] UNIV WESTERN AUSTRALIA,DEPT CHEM,NEDLANDS,WA 6009,AUSTRALIA

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1993年 / 46卷 / 01期

关键词：

D O I：

10.1071/CH9930073

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of chiral (2S)- and (2R)-4-methyleneoxazolidin-5-ones, in high enantiomeric purity from (S)-S-methylcysteine, and their highly exo-selective Diels-Alder reactions with cyclic dienes are described. (1R,2S,4S)-2-Aminobicyclo[2.2.1]heptane-2-carboxylic acid has been prepared in 92% e.e. by these methods. A number of the products have been characterized by single-crystal X-ray methods, and their structure systematics examined.

引用

页码：73 / 93

页数：21

共 20 条

[1] STEREOCHEMISTRY .60. KINETIC CONTROL OF ASYMMETRIC INDUCTION DURING OXAZOLIDINE FORMATION FROM (-)-EPHEDRINE AND AROMATIC-ALDEHYDES
AGAMI, C
RIZK, T
[J]. TETRAHEDRON, 1985, 41 (03) : 537 - 540
[2] DIASTEREOSELECTIVE RADICAL-ADDITION TO DERIVATIVES OF DEHYDROALANINE AND OF DEHYDROLACTIC ACID
BECKWITH, ALJ
CHAI, CLL
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (16) : 1087 - 1088
[3] Carraher C.E., 1985, BIOACTIVE POLYM SYST
[4] ASYMMETRIC-SYNTHESIS OF 2-AMINONORBORNANE-2-CARBOXYLIC ACIDS BY DIELS-ALDER REACTION
CATIVIELA, C
LOPEZ, P
MAYORAL, JA
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (12) : 1295 - 1304
[5] A NEW HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF 2,5-DISUBSTITUTED-1,3-DIOXOLAN-4-ONES FROM ALPHA-HYDROXYACIDS
CHAPEL, N
GREINER, A
ORTHOLAND, JY
[J]. TETRAHEDRON LETTERS, 1991, 32 (11) : 1441 - 1442
[6] CHRISTENSEN HN, 1969, J BIOL CHEM, V224, P1510
[7] A CONVENIENT METHOD FOR THE SYNTHESIS OF BETA-SUBSTITUTED ALPHA-AMINO-ACIDS - DIASTEREOSELECTIVE CONJUGATE ADDITION OF NITRONATES TO A CHIRAL DEHYDROALANINE DERIVATIVE
CROSSLEY, MJ
TANSEY, CW
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1992, 45 (02) : 479 - 481
[8] STUDIES DIRECTED TOWARDS THE TOTAL SYNTHESIS OF ANTICAPSIN - X-RAY CRYSTAL-STRUCTURE OF (1RS,2SR,4RS,5RS,6SR)-5-HYDROXY-2-PHTHALIMIDO-1-TRIMETHYLSILYLOXY-BICYCLO[2.2.2]OCTANE-2,6-CARBOLACTONE
CROSSLEY, MJ
HAMBLEY, TW
STAMFORD, AW
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (11) : 1827 - 1837
[9] ALPHA-ALKYLATION OF ACYCLIC AMINO-ACIDS WITH SELF-REPRODUCTION OF THE CENTER OF CHIRALITY - A NEW ROUTE TO (S)-(+)-ALPHA-ALKYLATED ASPARTIC ACIDS
FADEL, A
SALAUN, J
[J]. TETRAHEDRON LETTERS, 1987, 28 (20) : 2243 - 2246
[10] DRAMATIC RATE ACCELERATIONS OF DIELS-ALDER REACTIONS IN 5-M LITHIUM PERCHLORATE DIETHYL-ETHER - THE CANTHARIDIN PROBLEM REEXAMINED
GRIECO, PA
NUNES, JJ
GAUL, MD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) : 4595 - 4596

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