β-Peptides as catalysts:: poly-β-leucine as a catalyst for the Julia-Colonna asymmetric epoxidation of enones

被引：35

作者：

Coffey, PE

Drauz, KH

Roberts, SM ^{[1
]}

Skidmore, J

Smith, JA

机构：

[1] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

[2] Degussa Huls AG, D-63457 Hanau, Germany

[3] Univ Liverpool, Sch Biol Sci, Liverpool L69 7ZB, Merseyside, England

来源：

CHEMICAL COMMUNICATIONS | 2001年 / 22期

关键词：

D O I：

10.1039/b106368p

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Poly-beta -leucines have been evaluated as catalysts for the Julia-Colonna asymmetric epoxidation of enones; the beta (3) isomer was found to be an effective catalyst for the epoxidation of chalcone (70% ee) and some analogues.

引用

页码：2330 / 2331

页数：2

共 20 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]

[Anonymous], 1987, Alpha-Aminoacid-N-Carboxy-Anhydrides and Related Heterocycles

[4] 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

[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] CONFORMATIONAL STUDIES OF POLY[(S)-BETA-AMINOBUTYRIC ACID] [J].

CHEN, F ;

LEPORE, G ;

GOODMAN, M .

MACROMOLECULES, 1974, 7 (06) :779-783

[7] Synthesis of optically active β-amino acid N-carboxyanhydrides [J].

Cheng, JJ ;

Ziller, JW ;

Deming, TJ .

ORGANIC LETTERS, 2000, 2 (13) :1943-1946

[8] Conformation and crystal structure of poly(alpha-cycloalkyl-beta-L-aspartate)s [J].

GarciaAlvarez, M ;

deIlarduya, AM ;

Leon, S ;

Aleman, C ;

MunozGuerra, S .

JOURNAL OF PHYSICAL CHEMISTRY A, 1997, 101 (23) :4215-4223

[9] Foldamers: A manifesto [J].

Gellman, SH .

ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (04) :173-180

[10]

GLICKSON JD, 1971, J AM CHEM SOC, V93, P3276

← 1 2 →