Reductive coupling of phthalic anhydrides with aliphatic ketones by low-valent titanium: Unusual two-to-one coupling for preparation of 3,3-disubstituted phthalides

Shota Yamamoto,Naoki Kise,Toshihiko Sakurai

doi:10.1016/j.tet.2019.130820

Reductive coupling of phthalic anhydrides with aliphatic ketones by low-valent titanium: Unusual two-to-one coupling for preparation of 3,3-disubstituted phthalides

Shota Yamamoto, Naoki Kise + Show 1 more

https://doi.org/10.1016/j.tet.2019.130820

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Journal: Tetrahedron	Publication Date: Nov 28, 2019
Citations: 7

Affiliation: Tottori University

#Coupling Of Anhydrides #Low-valent Titanium + Show 3 more

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Abstract

The reductive coupling of phthalic anhydrides with acetone by Zn-TiCl4 in THF gave two-to-one and one-to-one coupled products. The coupled products were transformed to 3,3-diisopropyl-, 3-isopropylidene-, and 3-isopropylphthalides. In addition, the reductive coupling of phthalic anhydrides with acetonylacetone by Zn-TiCl4 in THF gave 3-spirocyclopentanylphtalides stereoselectively.

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