Polyamino acid-catalysed asymmetric epoxidation: Sodium percarbonate as a source of base and oxidant

被引：53

作者：

Allen, JV

Drauz, KH

Flood, RW

Roberts, SM

Skidmore, J

机构：

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

[2] Degussa Huls AG, D-63403 Hanau, Germany

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 29期

关键词：

asymmetric reactions; enones; epoxidation; peptides and polypeptides;

D O I：

10.1016/S0040-4039(99)01021-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New reaction conditions, using sodium percarbonate, are reported for the polyamino acid-catalysed asymmetric epoxidation of enones. Under these new conditions the rate of the uncatalysed reaction is reduced allowing an increased ratio of substrate to catalyst compared with previous protocols. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5417 / 5420

页数：4

共 13 条

[1] Improved procedure for Julia-Colonna asymmetric epoxidation of α,β-unsaturated ketones:: total synthesis of diltiazem and Taxol™ side-chain
Adger, BM
Barkley, JV
Bergeron, S
Cappi, MW
Flowerdew, BE
Jackson, MP
McCague, R
Nugent, TC
Roberts, SM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (23): : 3501 - 3507
[2] SODIUM PERCARBONATE (SPC) AS A HYDROGEN-PEROXIDE SOURCE FOR ORGANIC-SYNTHESIS
ANDO, T
CORK, DG
KIMURA, T
[J]. CHEMISTRY LETTERS, 1986, (05) : 665 - 666
[3] BENTLEY P, UNPUB
[4] Towards a mechanistic insight into the Julia-Colonna asymmetric epoxidation of α, β-unsaturated ketones using discrete lengths of poly-leucine.
Bentley, PA
Cappi, MW
Flood, RW
Roberts, SM
Smith, JA
[J]. TETRAHEDRON LETTERS, 1998, 39 (50) : 9297 - 9300
[5] New procedures for the Julia-Colonna asymmetric epoxidation: synthesis of (+)-clausenamide
Cappi, MW
Chen, WP
Flood, RW
Liao, YW
Roberts, SM
Skidmore, J
Smith, JA
Williamson, NM
[J]. CHEMICAL COMMUNICATIONS, 1998, (10) : 1159 - 1160
[6] OXIDATION REACTIONS USING UREA HYDROGEN-PEROXIDE - A SAFE ALTERNATIVE TO ANHYDROUS HYDROGEN-PEROXIDE
COOPER, MS
HEANEY, H
NEWBOLD, AJ
SANDERSON, WR
[J]. SYNLETT, 1990, (09) : 533 - 535
[7] Synthetic applications of polymeric alpha-amino acids
Ebrahim, S
Wills, M
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (19) : 3163 - 3173
[8] POLYMER-SUPPORTED POLY(AMINO ACIDS) AS NEW ASYMMETRIC EPOXIDATION CATALYST OF ALPHA,BETA-UNSATURATED KETONES
ITSUNO, S
SAKAKURA, M
ITO, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (24) : 6047 - 6049
[9] "Synthetic Enzymes". Highly Stereoselective Epoxidation of Chalcone in a Triphasic Toluene-Water-Poly[(S)-alanine] System
Julia, S.
Vega, J. C.
[J]. AFINIDAD, 2024, 81 (603) : 929 - 931
[10] Development of the Julia asymmetric epoxidation reaction .1. Application of the oxidation to enones other than chalcones
LasterraSanchez, ME
Felfer, U
Mayon, P
Roberts, SM
Thornton, SR
Todd, CJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (04): : 343 - 348

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