The Diels-Alder reactions of polymer bound dehydroalanine derivatives

被引:16
作者
Burkett, BA [1 ]
Chai, CLL [1 ]
机构
[1] Australian Natl Univ, Res Sch Chem, Canberra, ACT 0200, Australia
关键词
dehydro amino acids; Diels-Alder; solid phase;
D O I
10.1016/S0040-4039(99)01451-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis and Dials-Alder cycloadditions of a number of polymer bound dehydroalanine derivatives are described. The studies compare methodologies for accessing polymer bound dehydroalanines and establish the versatility and efficiency of solid phase Diels-Alder reactions in the synthesis of carbocyclic amino acids. These studies nicely complement the growing repertoire of methodologies for the functionalisation of amino acid derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7035 / 7038
页数:4
相关论文
共 15 条
[1]   Rapid solid phase synthesis of α-amino acids [J].
Barbaste, M ;
Rolland-Fulcrand, V ;
Roumestant, ML ;
Viallefont, P ;
Martinez, J .
TETRAHEDRON LETTERS, 1998, 39 (35) :6287-6290
[2]   SOLID-PHASE SYNTHESIS OF SELECTIVELY PROTECTED PEPTIDES FOR USE AS BUILDING UNITS IN SOLID-PHASE SYNTHESIS OF LARGE MOLECULES [J].
BARTON, MA ;
LEMIEUX, RU ;
SAVOIE, JY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (14) :4501-4506
[3]  
Brown RCD, 1998, J CHEM SOC PERK T 1, P3293
[4]   Unexpected variations in the reactivities and selectivities of acyclic and cyclic dehydrodipeptides in Diels-Alder reactions [J].
Burkett, BA ;
Chai, CLL ;
Hockless, DCR .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1998, 51 (11) :993-997
[5]  
BURKETT BA, UNPUB
[6]   RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].
DUTHALER, RO .
TETRAHEDRON, 1994, 50 (06) :1539-1650
[7]   STUDY OF THE INFLUENCE OF ULTRASOUND AND AQUEOUS SOLVENT ON THE DIELS-ALDER REACTION - THE CASE OF CYCLOPENTADIENE AND ACETAMIDOACRYLATES [J].
ELGUERO, J ;
GOYA, P ;
PAEZ, JA .
SYNTHETIC COMMUNICATIONS, 1989, 19 (3-4) :473-476
[8]   BIARYL SYNTHESIS VIA SUZUKI COUPLING ON A SOLID SUPPORT [J].
FRENETTE, R ;
FRIESEN, RW .
TETRAHEDRON LETTERS, 1994, 35 (49) :9177-9180
[9]   Photoacoustic FTIR spectroscopy, a nondestructive method for sensitive analysis of solid-phase organic chemistry [J].
Gosselin, F ;
DiRenzo, M ;
Ellis, TH ;
Lubell, WD .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :7980-7981
[10]   A SYNTHESIS OF 2-AMINONORBORNENE-2-CARBOXYLIC ACID-DERIVATIVES BY DIELS-ALDER REACTION USING ALPHA,BETA-DEHYDROALANINATES AS A DIENOPHILE [J].
HORIKAWA, H ;
NISHITANI, T ;
IWASAKI, T ;
MUSHIKA, Y ;
INOUE, I ;
MIYOSHI, M .
TETRAHEDRON LETTERS, 1980, 21 (42) :4101-4104