Stereoselective synthesis of ferrocenylamino acids

被引:13
作者
Adamczyk, M [1 ]
Reddy, RE [1 ]
Rege, SD [1 ]
机构
[1] Abbott Labs, Div Diagnost, Div Organ Chem Res 9NM AP20, Abbott Pk, IL 60064 USA
关键词
D O I
10.1080/00397910008087166
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantiopure ferrocenyl-beta, and bis-beta-amino acids [(R)-(+)-1 and (R,R)-(+)-2] were prepared from (S)-(+)-sulfinimine (3) and (S,S)(+)-bis-sulfinimine (4) respectively. The desired sulfinimines [(S)-(+)-3 and (S,S)-(+)-4] Mere prepared from (S)-Andersen reagent (5) and ferrocenecarboxaldehyde (6) and 1,1'-ferrocenedicarboxaldehyde (7).
引用
收藏
页码:1389 / 1400
页数:12
相关论文
共 35 条
[21]   CONTINUOUS ELECTROCHEMICAL ACTIVATION OF FLAVOENZYMES USING POLYETHYLENEGLYCOL-BOUND FERROCENES AS MEDIATORS - A MODEL FOR THE APPLICATION OF OXIDOREDUCTASES AS OXIDATION CATALYSTS IN ORGANIC-SYNTHESIS [J].
FREDE, M ;
STECKHAN, E .
TETRAHEDRON LETTERS, 1991, 32 (38) :5063-5066
[22]   CRYSTAL ENVIRONMENTS AND GEOMETRIES OF LEUCINE, ISOLEUCINE, VALINE, AND PHENYLALANINE PROVIDE ESTIMATES OF MINIMUM NONBONDED CONTACT AND PREFERRED VANDERWAALS INTERACTION DISTANCES [J].
GOULD, RO ;
GRAY, AM ;
TAYLOR, P ;
WALKINSHAW, MD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (21) :5921-5927
[23]   Aggregation of ferrocene pendant groups along the backbone of DNA for a supramolecular redox system [J].
Hirao, T ;
Nomoto, A ;
Yamazaki, S ;
Ogawa, A ;
Moriuchi, T .
TETRAHEDRON LETTERS, 1998, 39 (24) :4295-4298
[24]  
Hruby V J, 1994, Methods Mol Biol, V35, P201
[25]  
Juaristi E., 1997, ENANTIOSELECTIVE SYN
[26]  
Kagan H.B., 1997, Advances in Asymmetric Synthesis, VVolume 2, P189
[27]   Glucose oxidase electrodes via reconstitution of the apo-enzyme:: tailoring of novel glucose biosensors [J].
Katz, E ;
Riklin, A ;
Heleg-Shabtai, V ;
Willner, I ;
Bückmann, AF .
ANALYTICA CHIMICA ACTA, 1999, 385 (1-3) :45-58
[28]   Chiral sulfur-containing 1,2-disubstituted ferrocenes [J].
Lagneau, NM ;
Chen, Y ;
Robben, PM ;
Sin, HS ;
Takasu, K ;
Chen, JS ;
Robinson, PD ;
Hua, DH .
TETRAHEDRON, 1998, 54 (26) :7301-7334
[29]   Enantioselective synthesis and use in catalytic asymmetric addition of diethylzinc to benzaldehyde of new chiral cyclic hydroxyamino ferrocene and chromium complexes:: influence of the complexation on the enantioselectivity [J].
Malfait, S ;
Pélinski, L ;
Brocard, J .
TETRAHEDRON-ASYMMETRY, 1998, 9 (15) :2595-2610
[30]   Tethered mediator biosensor. Mediated electron transfer between redox enzyme and electrode via ferrocene anchored to electrode surface with long poly(oxyethylene) chain [J].
Okawa, Y ;
Nagano, M ;
Hirota, S ;
Kobayashi, H ;
Ohno, T ;
Watanabe, M .
BIOSENSORS & BIOELECTRONICS, 1999, 14 (02) :229-235