CYCLOPENTADIENES AS CHIRAL TEMPLATES .4. AN EASY ACCESS TO (S)-HYDROXYCYCLOHEXENONE AND (R)-HYDROXYCYCLOHEXENONE

被引：21

作者：

BRUNJES, R ^{[1
]}

TILSTAM, U ^{[1
]}

WINTERFELDT, E ^{[1
]}

机构：

[1] UNIV HANNOVER,INST ORGAN CHEM,SCHNEIDERBERG 1B,W-3000 HANNOVER 1,GERMANY

来源：

CHEMISCHE BERICHTE | 1991年 / 124卷 / 07期

关键词：

CYCLOPENTADIENES; CHIRAL; QUINONE ADDUCTS; DIELS-ALDER REACTIONS; PURE;

D O I：

10.1002/cber.19911240732

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Diels-Alder adduct obtained by addition of quinone to the chiral cyclopentadiene 2 undergoes regioselective and stereoselective reduction after hydrogenation. The 4-hydroxy ketone 3 thus formed yields the title compound 1 in a thermal retro Diels-Alder process.

引用

页码：1677 / 1678

页数：2

共 5 条

[1] SYNTHESIS OF 2 USEFUL, ENANTIOMERICALLY PURE DERIVATIVES OF (S)-4-HYDROXY-2-CYCLOHEXENONE
AUDIA, JE
BOISVERT, L
PATTEN, AD
VILLALOBOS, A
DANISHEFSKY, SJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) : 3738 - 3740
[2] PURE ENANTIOMERS FROM RETRO-DIELS-ALDER PROCESSES
BECKMANN, M
HILDEBRANDT, H
WINTERFELDT, E
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (05) : 335 - 345
[3] ESSIG S, 1991, CHIMIA, V45, P30
[4] GARRENO MC, 1990, TETRAHEDRON LETT, V31, P6653
[5] MATCHEVA K, 1989, SYNTHESIS-STUTTGART, P814

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