CHEMOSELECTIVE RHODIUM-CARBENOID REACTION WITH THE AROMATIC NUCLEUS -AN EFFICIENT METHODOLOGY FOR 2-INDANONES, 2-TETRALONES AND 2-BENZOSUBERONES AND ITS APPLICATION IN THE SYNTHESIS OF (+ -)-AR-HIMACHALENE/
Sg. Sudrik et al., CHEMOSELECTIVE RHODIUM-CARBENOID REACTION WITH THE AROMATIC NUCLEUS -AN EFFICIENT METHODOLOGY FOR 2-INDANONES, 2-TETRALONES AND 2-BENZOSUBERONES AND ITS APPLICATION IN THE SYNTHESIS OF (+ -)-AR-HIMACHALENE/, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 36(12), 1997, pp. 1103-1112
Rhodium-carbenoid species derived from rhodium acetate-catalyzed decom
position of aryl alkyl alpha-diazoketones have been shown to display a
chemoselective addition into the aromatic nucleus, instead of inserti
on into an aliphatic C-H site. The synthetic utility of this chemosele
ctive reaction is exemplified by the preparation of substituted fused
aromatic systems such as 2-indanones, 2-tetralones and 2-benzosuberone
s. In addition, a short and efficient synthesis of (+/-)-ar-Himachalen
e, a naturally occurring sesquiterpene is realized.