A HIGHLY STEREOSELECTIVE SYNTHESIS OF A TETRAHYDROFLUORENE VIA A DOMINO CLAISEN REARRANGEMENT HETERO-ENE REACTION

Authors
LAMBRECHT S SCHAFER HJ FROHLICH R GREHL M
Citation
S. Lambrecht et al., A HIGHLY STEREOSELECTIVE SYNTHESIS OF A TETRAHYDROFLUORENE VIA A DOMINO CLAISEN REARRANGEMENT HETERO-ENE REACTION, Synlett, (3), 1996, pp. 283
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
3
Year of publication
1996
Database
ISI
SICI code
0936-5214(1996):3<283:AHSSOA>2.0.ZU;2-C
Abstract
3-(Cyclohex-2-enyloxy)-4-methoxybenzaldehyde (2) is converted in high yield to ,8aS,9S)-tetrahydro-3-methoxy-5H-fluorene-4,9-diol (4) via a domino Claisen rearrangement hetero-ene reaction. With the correspondi ng acetal of aldehyde 2 the reaction ends after the Claisen rearrangem ent and -(cyclohex-2-enyl)-3-hydroxy-4-methoxybenzaldehyde is obtained after hydrolysis.