Gram-Scale Robust Synthesis of 1-Chloro-2,3-dimethyl-4-phenylnaphthalene: A Promising Scaffold with Three Contiguous Reaction Positions

Abstract A three-step reaction sequence for the gram-scale synthesis of 1-chloro-2,3-dimethyl-4-phenylnaphthalene was developed. (i) Stereoselective dichlorocarbene addition to methyl angelate afforded methyl (1 S *,3 S *)-2,2-dichloro-1,3-dimethylcyclopropane-1-carboxylate (78% yield, >98% purit...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2020-12, Vol.52 (24), p.3811-3817
Main Authors: Moriguchi, Kento, Kono, Taro, Seko, Shinzo, Tanabe, Yoo
Format: Article
Language:English
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psp
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Summary:Abstract A three-step reaction sequence for the gram-scale synthesis of 1-chloro-2,3-dimethyl-4-phenylnaphthalene was developed. (i) Stereoselective dichlorocarbene addition to methyl angelate afforded methyl (1 S *,3 S *)-2,2-dichloro-1,3-dimethylcyclopropane-1-carboxylate (78% yield, >98% purity, distillation). (ii) Addition reaction of two molar amounts of PhLi afforded (1 S *,3 S *)-2,2-dichloro-1,3-dimethylcyclopropyldiphenylmethanol (81% yield, >98% purity, recrystallization). (iii) Key SnCl 4 -mediated benzannulation produced the desired product (83% yield, >98% purity, recrystallization) with three contiguous reaction sites. Five derivatization examples including benzylic reactions and cross-couplings at the pendant Cl-position are demonstrated. Some relevant distinctive benzannulations are also discussed.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0040-1706471