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Stereoselective synthesis of 1,3-disubstituted phthalans by cyclization of (1S)-1-{2-[hydroxy(diaryl)methyl]phenyl}ethanols

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Abstract

Cyclization of pure enantiomers of 1-{2-[hydroxy(diaryl)methyl]phenyl}ethanol proceeds stereoselectively and affords 1,3-disubstituted 1,3-dihydroisobenzofurans (phthalans) in moderate-to-high enantiomeric (81.7% ee) or diastereomeric (72% de) purity.

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Authors and Affiliations

  1. Chemical department, M. V. Lomonosov Moscow State University, 1/3 Leninskie Gory, Moscow, 119991, Russian Federation

    I. N. Shishkina, E. Yu. Sokolovskaya & V. M. Demyanovich

Authors
  1. I. N. Shishkina
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  2. E. Yu. Sokolovskaya
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  3. V. M. Demyanovich
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Correspondence to V. M. Demyanovich.

Additional information

Based on the materials of the International Congress on the Heterocyclic Chemistry "KOST-2015" (October 17—23, 2015, Moscow, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2229—2232, September, 2016.

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Shishkina, I.N., Sokolovskaya, E.Y. & Demyanovich, V.M. Stereoselective synthesis of 1,3-disubstituted phthalans by cyclization of (1S)-1-{2-[hydroxy(diaryl)methyl]phenyl}ethanols. Russ Chem Bull 65, 2229–2232 (2016). https://doi.org/10.1007/s11172-016-1573-y

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  • DOI: https://doi.org/10.1007/s11172-016-1573-y

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