Development of the Julia-Colonna asymmetric epoxidation reaction: Part 1. Preparation and activation of the polyleucine catalyst

被引:32
作者
Baars, S
Drauz, KH
Krimmer, HP
Roberts, SM
Sander, J
Skidmore, J
Zanardi, G
机构
[1] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England
[2] Degussa AG, D-63457 Hanau, Germany
关键词
D O I
10.1021/op0300037
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The preparation of silica-supported poly-L-leucine has been studied under a variety of reaction conditions leading to an efficient procedure for the preparation of material suitable for use in the Julia-Colonna asymmetric epoxidation reaction.
引用
收藏
页码:509 / 513
页数:5
相关论文
共 30 条
[1]   Improved procedure for Julia-Colonna asymmetric epoxidation of α,β-unsaturated ketones:: total synthesis of diltiazem and Taxol™ side-chain [J].
Adger, BM ;
Barkley, JV ;
Bergeron, S ;
Cappi, MW ;
Flowerdew, BE ;
Jackson, MP ;
McCague, R ;
Nugent, TC ;
Roberts, SM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (23) :3501-3507
[2]   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
[3]   Asymmetric epoxidation of a geminally-disubstituted and some trisubstituted enones catalysed by poly-L-leucine [J].
Bentley, PA ;
Bickley, JF ;
Roberts, SM ;
Steiner, A .
TETRAHEDRON LETTERS, 2001, 42 (22) :3741-3743
[4]  
BULMANPAGE PC, 2001, J ORG CHEM, V66, P6926
[5]   New procedures for the Julia-Colonna asymmetric epoxidation: synthesis of (+)-clausenamide [J].
Cappi, MW ;
Chen, WP ;
Flood, RW ;
Liao, YW ;
Roberts, SM ;
Skidmore, J ;
Smith, JA ;
Williamson, NM .
CHEMICAL COMMUNICATIONS, 1998, (10) :1159-1160
[6]   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
[7]   Stereocontrolled ring-opening of some enantiomerically enriched epoxy ketones and epoxy alcohols using trimethylaluminium:: synthesis of (S)-2-arylpropanoic acids [J].
Carde, L ;
Davies, DH ;
Roberts, SM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (15) :2455-2463
[8]   Asymmetric epoxidation of α,β-unsaturated ketones catalyzed by chiral ytterbium complexes [J].
Chen, RF ;
Qian, CT ;
de Vries, JG .
TETRAHEDRON LETTERS, 2001, 42 (39) :6919-6921
[9]   Julia-Colonna asymmetric epoxidation of furyl styryl ketone as a route to intermediates to naturally-occurring styryl lactones [J].
Chen, WP ;
Roberts, SM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (02) :103-105
[10]   SYNTHETIC POLYPEPTIDES .3. INITIATORS FOR THE CO-POLYMERISATION OF OXAZOLID-2-5-DIONES [J].
COLEMAN, D .
JOURNAL OF THE CHEMICAL SOCIETY, 1950, (NOV) :3222-3229