Ytterbium(III) trifluoromethanesulfonate catalyzed high pressure reaction of epoxides with indole. An enantioselective synthesis of (+)-diolmycin A2

被引：63

作者：

Kotsuki, H

Teraguchi, M

Shimomoto, N

Ochi, M

机构：

[1] Department of Chemistry, Faculty of Science, Kochi University, Kochi 780, Akebono-cho

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 21期

关键词：

D O I：

10.1016/0040-4039(96)00670-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Epoxide opening reactions with indole are efficiently accelerated under high pressure conditions in the presence of a catalytic amount of ytterbium(III) trifluoromethanesulfonate to afford tryptophol derivatives. The procedure is successfully applied for an enantioselective synthesis of (+)-diolmycin A2. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：3727 / 3730

页数：4

共 20 条

[1] A SULFINYL TRIALKOXYCARBONYL ETHENE AS A NEW ENANTIOPURE DIENOPHILE IN ASYMMETRIC DIELS-ALDER REACTIONS
CARRETERO, JC
RUANO, JLG
CABREJAS, LMM
[J]. TETRAHEDRON, 1995, 51 (30) : 8323 - 8332
[2] LANTHANIDE(III) TRIFLUOROMETHANESULFONATES AS EXTRAORDINARILY EFFECTIVE NEW CATALYSTS FOR THE AMINOLYSIS OF 1,2-EPOXIDES
CHINI, M
CROTTI, P
FAVERO, L
MACCHIA, F
PINESCHI, M
[J]. TETRAHEDRON LETTERS, 1994, 35 (03) : 433 - 436
[3] AMINOLYSIS OF OXETANES - QUITE EFFICIENT CATALYSIS BY LANTHANIDE(III) TRIFLUOROMETHANSULFONATES
CROTTI, P
FAVERO, L
MACCHIA, F
PINESCHI, M
[J]. TETRAHEDRON LETTERS, 1994, 35 (38) : 7089 - 7092
[4] CATALYTIC HIGH-PRESSURE SYNTHESIS OF HINDERED BETA-AMINOESTERS
JENNER, G
[J]. TETRAHEDRON LETTERS, 1995, 36 (02) : 233 - 236
[5] KOBAYASHI S, 1994, SYNLETT, P689
[6] KOBAYASHI S, 1995, YUKI GOSEI KAGAKU KY, V53, P370
[7] High-pressure organic chemistry .19. High-pressure-promoted, silica gel-catalyzed reaction of epoxides with nitrogen heterocycles
Kotsuki, H
Hayashida, K
Shimanouchi, T
Nishizawa, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03) : 984 - 990
[8] HIGH-PRESSURE ORGANIC-CHEMISTRY .10. NOVEL NEUTRAL ALKYLATIONS OF INDOLES AND PYRROLES WITH VINYL EPOXIDES AT HIGH-PRESSURE
KOTSUKI, H
NISHIUCHI, M
KOBAYASHI, S
NISHIZAWA, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) : 2969 - 2972
[9] A NOVEL CARBON CARBON BOND-FORMING REACTION OF TRIFLATES WITH COPPER(I)-CATALYZED GRIGNARD-REAGENTS - A NEW CONCISE AND ENANTIOSPECIFIC SYNTHESIS OF (+)-EXO-BREVICOMIN, (5R,6S)-(-)-6-ACETOXY-5-HEXADECANOLIDE, AND L-FACTOR
KOTSUKI, H
KADOTA, I
OCHI, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (14) : 4417 - 4422
[10] SYNTHESIS OF NOVEL CHIRAL DIAZOLE LIGANDS FOR ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO BENZALDEHYDE
KOTSUKI, H
HAYAKAWA, H
WAKAO, M
SHIMANOUCHI, T
OCHI, M
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (11) : 2665 - 2668

← 1 2 →