Synthesis of 3,4,5-trisubstituted cyclohexanones by cycloaddition to solid phase 2-aminobutadienes

被引：29

作者：

Crawshaw, M

Hird, NW

Irie, K

Nagai, K

机构：

[1] SMITHKLINE BEECHAM PHARMACEUT,HARLOW CM19 5AD,ESSEX,ENGLAND

[2] TAKEDA CHEM IND LTD,YODOGAWA KU,OSAKA 53,JAPAN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 40期

关键词：

D O I：

10.1016/S0040-4039(97)01634-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[4+2] Cycloaddition of maleimides and nitrostyrenes to resin bound 4-substituted-2-aminobutadienes gives, after cleavage, 3,4,5-trisubstituted cyclohexanones in moderate to good yields and high purities. The reaction occurs under mild conditions and has been automated on the ACT 496 synthesiser. (C) 1997 Elsevier Science Ltd.

引用

页码：7115 / 7118

页数：4

共 10 条

[1] 2-AMINO-1,3-BUTADIENES AS CHIRAL BUILDING-BLOCKS - ENANTIOSELECTIVE SYNTHESIS OF 4-PIPERIDONES, 4-NITROCYCLOHEXANONES, AND 1,3-CYCLOHEPTADIONE DERIVATIVES
BARLUENGA, J
AZNAR, F
VALDES, C
MARTIN, A
GARCIAGRANDA, S
MARTIN, E
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) : 4403 - 4404
[2] SUBSTITUENT EFFECTS ON THE REACTIVITY OF 2-MORPHOLINOBUTADIENES IN THE PRESENCE OF DIENOPHILES
BARLUENGA, J
AZNAR, F
CABAL, MP
VALDES, C
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (03): : 633 - 638
[3] ENDERS D, 1994, SYNTHESIS-STUTTGART, P66
[4] ENDERS D, 1992, SYNTHESIS-STUTTGART, P1242
[5] Fringuelli F., 1990, DIENES DIELSALDER RE
[6] HENKE S, 1996, IBC COMB CHEM AUT C
[7] CHIRAL 2-AMINO-1,3-BUTADIENES - NEW REAGENTS FOR ASYMMETRIC CYCLOADDITIONS
KROHN, K
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (11): : 1582 - 1584
[8] Diastereoselective Diels-Alder reactions of nonracemic 3- and 4-amino furans bound to polystyrene. A comparison of these reactions to their solution state analogues.
Schlessinger, RH
Bergstrom, CP
[J]. TETRAHEDRON LETTERS, 1996, 37 (13) : 2133 - 2136
[9] Tietze LF, 1996, SYNLETT, P1043
[10] THE USE OF POLYMER SUPPORTS IN ORGANIC-SYNTHESIS .22. REGIOSELECTIVITY IN CYCLOADDITION REACTIONS ON SOLID-PHASES
YEDIDIA, V
LEZNOFF, CC
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1980, 58 (11): : 1144 - 1150

← 1 →