Abstract
The gold(I)-catalyzed hydroarylation of cyclohexa-1,3-dienes bearing an aryl group and a gem-diester in the tether proceeds in a 1,4-addition manner and in a diastereoselective fashion to afford perhydrophenanthrene rings. The reaction proceeded via attack of the aryl group onto the gold-activated cyclic dienes followed by rearomatization and protodeauration to generate perhydrophenanthrenes in good yields. This hydroarylation can be applied to the synthesis of perhydrocyclohepta[a]naphthalenes from aryl-tethered cycloheptadienes and the gold(I) catalyst.
Original language | English |
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Pages (from-to) | 4027-4033 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 76 |
Issue number | 10 |
DOIs | |
Publication status | Published - 2011 May 20 |
ASJC Scopus subject areas
- Organic Chemistry