Michael–Michael Ring-Closure Reactions for a Dihapto-Coordinated Naphthalene Complex of Molybdenum
Organometallics(2020)
Abstract
The complex MoTp(NO)(DMAP)(η2-naphthalene) (1; DMAP = 4-(dimethylamino)pyridine; Tp = tris(pyrazolyl)borate) is demonstrated to undergo Michael–Michael ring-closure (MIMIRC) reactions promoted by trimethylsilyltriflate. The resulting hexahydrophenanthrenes are formed stereoselectively, with isolation of a single dominant isomer. Combining the MIMIRC sequence with an oxidative decomplexation step, the final tricyclics can be synthesized from the naphthalene complex with overall yields between 19 and 50% (for four steps). This reaction sequence is shown to be capable of producing a steroidal core directly from naphthalene, providing access to a biologically relevant carbon framework.
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Key words
molybdenum,reactions,ring-closure,dihapto-coordinated
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