
Phosphorus, Sulfur and Silicon and the Related Elements p. 181 - 189 (2000)
Update date:2022-08-05
Topics:
Hajipour
Hantehzadeh
The addition of the lithium carbanion of (R)-(+)-3,4-dimethoxybenzyl 2-methoxy-1-naphthyl sulfoxide 3 to cyclic nitrone 4, under kinetically controlled conditions gave isoquinoline sulfoxide derivatives 5 and 6 in high diastereoselectivities. Under equilibrium controlled conditions poor diastereoselectivity results. The chiral (R)-(+)-3,4-dimethoxybenzyl 2-methoxy-1-naphthyl sulfoxide 3 was easily prepared by the reaction of 3,4-dimethoxybenzylmagnesium chloride 2 with (-)-(S) menthyl 2-methoxy-naphthalene sulfinate 1 in dry benzene. This methodology allows for the synthesis of the isoquinoline alkaloid (R)-(-)-norlaudanosine 8 in three efficient synthetic steps.
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