Efficient asymmetric epoxidation of α,β-unsaturated ketones using a soluble triblock polyethylene glycol-polyamino acid catalyst

被引:75
作者
Flood, RW [1 ]
Geller, TP [1 ]
Petty, SA [1 ]
Roberts, SM [1 ]
Skidmore, J [1 ]
Volk, M [1 ]
机构
[1] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England
关键词
D O I
10.1021/ol007005l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Polyethylene glycol (PEG)-bound poly-L leucine acts as a THF-soluble catalyst for the Julia-Colonna asymmetric epoxidation of enones, Excellent enantioselectivities may be obtained even with short chain length polyleucine. FT-IR investigations have determined that the catalytically active polyleucine components of these copolymers have an alpha -helical structure.
引用
收藏
页码:683 / 686
页数:4
相关论文
共 23 条
[1]   Polyamino acid-catalysed asymmetric epoxidation: Sodium percarbonate as a source of base and oxidant [J].
Allen, JV ;
Drauz, KH ;
Flood, RW ;
Roberts, SM ;
Skidmore, J .
TETRAHEDRON LETTERS, 1999, 40 (29) :5417-5420
[2]   QUANTITATIVE STUDIES OF THE STRUCTURE OF PROTEINS IN SOLUTION BY FOURIER-TRANSFORM INFRARED-SPECTROSCOPY [J].
ARRONDO, JLR ;
MUGA, A ;
CASTRESANA, J ;
GONI, FM .
PROGRESS IN BIOPHYSICS & MOLECULAR BIOLOGY, 1993, 59 (01) :23-56
[3]   Towards a mechanistic insight into the Julia-Colonna asymmetric epoxidation of α, β-unsaturated ketones using discrete lengths of poly-leucine. [J].
Bentley, PA ;
Cappi, MW ;
Flood, RW ;
Roberts, SM ;
Smith, JA .
TETRAHEDRON LETTERS, 1998, 39 (50) :9297-9300
[4]   Asymmetric epoxidation of enones employing polymeric alpha-amino acids in non-aqueous media [J].
Bentley, PA ;
Bergeron, S ;
Cappi, MW ;
Hibbs, DE ;
Hursthouse, MB ;
Nugent, TC ;
Pulido, R ;
Roberts, SM ;
Wu, LE .
CHEMICAL COMMUNICATIONS, 1997, (08) :739-740
[5]   PaaSicats:: Powerful catalysts for asymmetric epoxidation of enones.: Novel syntheses of α-arylpropanoic acids including (S)-fenoprofen [J].
Carde, L ;
Davies, H ;
Geller, TP ;
Roberts, SM .
TETRAHEDRON LETTERS, 1999, 40 (29) :5421-5424
[6]   INTENSITIES AND OTHER SPECTRAL PARAMETERS OF INFRARED AMIDE BANDS OF POLYPEPTIDES IN ALPHA-HELICAL FORM [J].
CHIRGADZE, YN ;
BRAZHNIKOV, EV .
BIOPOLYMERS, 1974, 13 (09) :1701-1712
[7]   INTENSITIES AND OTHER SPECTRAL PARAMETERS OF INFRARED AMIDE BANDS OF POLYPEPTIDES IN BETA- AND RANDOM FORMS [J].
CHIRGADZE, YN ;
SHESTOPALOV, BV ;
VENYAMINOV, SY .
BIOPOLYMERS, 1973, 12 (06) :1337-1351
[8]   SYNTHETIC ENZYMES .4. HIGHLY ENANTIOSELECTIVE EPOXIDATION BY MEANS OF POLYAMINOACIDS IN A TRIPHASE SYSTEM - INFLUENCE OF STRUCTURAL VARIATIONS WITHIN THE CATALYSTS [J].
COLONNA, S ;
MOLINARI, H ;
BANFI, S ;
JULIA, S ;
MASANA, J ;
ALVAREZ, A .
TETRAHEDRON, 1983, 39 (09) :1635-1641
[9]   A new procedure for the Julia-Colonna stereoselective epoxidation reaction under non-aqueous conditions: the development of a catalyst comprising polyamino acid on silica (PaaSiCat) [J].
Geller, T ;
Roberts, SM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (11) :1397-1398
[10]   The effects of chain length and thermal denaturation on helix-forming peptides: A mode-specific analysis using 2D FT-IR [J].
Graff, DK ;
PastranaRios, B ;
Venyaminov, SY ;
Prendergast, FG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (46) :11282-11294