THE PROLINE AND BETA-LACTOGLOBULIN MEDIATED ASYMMETRIC SELF-CONDENSATION OF BETA-IONYLIDENEACETALDEHYDE, RETINAL AND RELATED-COMPOUNDS

被引:23
作者
ASATO, AE
WATANABE, C
LI, XY
LIU, RSH
机构
[1] Department of Chemistry, University of Hawaii, Honolulu
关键词
D O I
10.1016/S0040-4039(00)79825-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Proline was found to effectively mediate the asymmetric reaction of beta-ionylideneacetaldehyde 1A, retinal and related alpha,beta-unsaturated aldehydes to form their corresponding self-condensation products in reasonable enantiomeric excess (up to 65% ee). This same interesting conversion was also observed when 1A was incubated in the presence of the milk whey protein beta-lactoglobulin (BLG).
引用
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页码:3105 / 3108
页数:4
相关论文
共 16 条
[1]  
Buchschacher P., 1985, ORG SYNTH, V63, P37
[2]  
COPPOLA GM, 1987, ASYMMETRIC SYNTHESIS, P267
[3]   SYNTHESIS OF OPTICALLY-ACTIVE COMPOUNDS - A LARGE-SCALE PERSPECTIVE [J].
CROSBY, J .
TETRAHEDRON, 1991, 47 (27) :4789-4846
[4]  
FISCHER FG, 1932, J LIEBIGS ANN, V494, P263
[5]   BETA-LACTOGLOBULIN DIRECTED PHOTOISOMERIZATION OF RETINAL AND RELATED-COMPOUNDS [J].
LI, XY ;
ASATO, AE ;
LIU, RSH .
TETRAHEDRON LETTERS, 1990, 31 (34) :4841-4844
[6]   VALENCE ISOMERIZATION OF A CIS-DIENONE TO AN ALPHA-PYRAN [J].
MARVELL, EN ;
CAPLE, G ;
GOSINK, TA ;
ZIMMER, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (03) :619-&
[7]   NEW GEOMETRIC ISOMERS OF VITAMIN-A .13. FLUORINATED RETINOIDS VIA CROSSED ALDOL CONDENSATION OF 1,1,1-TRIFLUOROACETONE [J].
MEAD, D ;
LOH, R ;
ASATO, AE ;
LIU, RSH .
TETRAHEDRON LETTERS, 1985, 26 (24) :2873-2876
[8]   MODEL COMPOUNDS FOR RHODOPSIN AND BACTERIORHODOPSIN - SYNTHESIS, AND H-1-NMR AND C-13-NMR STUDY [J].
RABILLER, C ;
DANHO, D .
HELVETICA CHIMICA ACTA, 1984, 67 (05) :1254-1273
[9]   PREPARATION OF STERICALLY HINDERED GEOMETRIC ISOMERS OF 7-CIS-BETA-IONYL AND BETA-IONYLIDENE DERIVATIVES IN VITAMIN-A SERIES [J].
RAMAMURTHY, V ;
TUSTIN, G ;
YAU, CC ;
LIU, RSH .
TETRAHEDRON, 1975, 31 (03) :193-199
[10]   Studies on ionone. II. Optical resolution of dl-alpha-ionone [J].
Sobotka, H ;
Bloch, E ;
Cahnmann, H ;
Feldbau, E ;
Rosen, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1943, 65 :2061-2062