Heterogeneous asymmetric aminohydroxylation of alkenes using a silica gel-supported bis-cinchona alkaloid

被引:24
作者
Song, CE
Oh, CR
Lee, SW
Lee, SG
Canali, L
Sherrington, DC
机构
[1] Korea Inst Sci & Technol, Div Appl Sci, Seoul 130650, South Korea
[2] Univ Strathclyde, Dept Pure & Appl Chem, Glasgow G1 1XL, Lanark, Scotland
关键词
D O I
10.1039/a806959j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Excellent enantioselectivities of up to > 99% ee have been achieved in the heterogeneous asymmetric aminohydroxylation of trans-cinnamate derivatives using silica gel-supported (QN)(2)PHAL [SGS-(QN)(2)PHAL 1]; the dark brown 1.0s complex, recovered by simple filtration after reaction, could be reused without any loss of enantioselectivity.
引用
收藏
页码:2435 / 2436
页数:2
相关论文
共 12 条
[1]   N-bromoacetamide - A new nitrogen source for the catalytic asymmetric aminohydroxylation of olefins [J].
Bruncko, M ;
Schlingloff, G ;
Sharpless, KB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14) :1483-1486
[2]  
Hoffmann A.W., 1881, Ber. Dtsch. Chem. Ges, V14, P2725
[3]   N-halocarbamate salts lead to more efficient catalytic asymmetric aminohydroxylation [J].
Li, GG ;
Angert, HH ;
Sharpless, KB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24) :2813-2817
[4]   Catalytic asymmetric aminohydroxylation provides a short taxol side-chain synthesis [J].
Li, GG ;
Sharpless, KB .
ACTA CHEMICA SCANDINAVICA, 1996, 50 (08) :649-651
[5]   Catalytic asymmetric aminohydroxylation (AA) of olefins [J].
Li, GG ;
Chang, HT ;
Sharpless, KB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (04) :451-454
[6]   Asymmetric aminohydroxylation of substituted styrenes using t-butyl carbamate [J].
O'Brien, P ;
Osborne, SA ;
Parker, DD .
TETRAHEDRON LETTERS, 1998, 39 (23) :4099-4102
[7]   N-chloro-N-sodio-2-trimethylsilyl ethyl carbamate:: A new nitrogen source for the catalytic asymmetric aminohydroxylation [J].
Reddy, KL ;
Dress, KR ;
Sharpless, KB .
TETRAHEDRON LETTERS, 1998, 39 (22) :3667-3670
[8]   From styrenes to enantiopure α-arylglycines in two steps [J].
Reddy, KL ;
Sharpless, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (06) :1207-1217
[9]   Smaller substituents on nitrogen facilitate the osmium-catalyzed asymmetric aminohydroxylation [J].
Rudolph, J ;
Sennhenn, PC ;
Vlaar, CP ;
Sharpless, KB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24) :2810-2813
[10]   Efficient and practical polymeric catalysts for heterogeneous asymmetric dihydroxylation of olefins [J].
Song, CE ;
Yang, JW ;
Ha, HJ ;
Lee, SG .
TETRAHEDRON-ASYMMETRY, 1996, 7 (03) :645-648