A STUDY OF ATYPICAL REACTION OF METHYL (TRIPHENYLPHOSPHORANYLIDENE)ACETATE WITH 3a-SUBSTITUTED BICYCLIC β-KETO-γ-SULTAMS

Authors

  • Taras V. Omelian 1) Enamine Ltd., 78 Chervonotkatska St., Kyiv 02660, Ukraine 2) Taras Shevchenko National University of Kyiv, 12 Lva Tolstoho St., Kyiv 01033, Ukraine
  • Pavlo O. Iegorov 1) Enamine Ltd., 78 Chervonotkatska St., Kyiv 02660, Ukraine 2) Taras Shevchenko National University of Kyiv, 12 Lva Tolstoho St., Kyiv 01033, Ukraine
  • Anton O. Poliudov 1) Enamine Ltd., 78 Chervonotkatska St., Kyiv 02660, Ukraine 3) National Technical University of Ukraine ''Igor Sikorsky Kyiv Polytechnic Institute'', 37 Peremohy Ave., Kyiv 03056, Ukraine
  • Alexey V. Dobrydnev 1) Enamine Ltd., 78 Chervonotkatska St., Kyiv 02660, Ukraine 2) Taras Shevchenko National University of Kyiv, 12 Lva Tolstoho St., Kyiv 01033, Ukraine
  • Eugeniy N. Ostapchuk 1) Enamine Ltd., 78 Chervonotkatska St., Kyiv 02660, Ukraine 2) Taras Shevchenko National University of Kyiv, 12 Lva Tolstoho St., Kyiv 01033, Ukraine
  • Yulian M. Volovenko Taras Shevchenko National University of Kyiv, 12 Lva Tolstoho St., Kyiv 01033, Ukraine

DOI:

https://doi.org/10.1007/5975

Keywords:

amino acids, phosphonium ylides, sulfonamides, acylation, CSIC reaction, cyclization, Wittig reaction.

Abstract

A number of 2-substituted 4–7-membered cyclic amino acid esters bearing endocyclic amino group were sequentially mesylated and cyclized via the CSIC reaction strategy to give the key precursors 3a-substituted bicyclic isothiazolidin-4-one 1,1-dioxides. Further reaction with methyl (triphenylphosphoranylidene)acetate afforded the corresponding 3a-substituted 2-[(triphenylphosphonio)acetyl]perhydro[1,2]thiazoloazahetaryl-3-olate 1,1-dioxides. The nature of the substituent at position 3a plays a crucial role in the reaction direction with this Wittig reagent. Specifically, 3a-unsubstituted counterpart participates in the classical course of the reaction providing the expected prototropic mixture of corresponding esters.

Author Biographies

Taras V. Omelian, 1) Enamine Ltd., 78 Chervonotkatska St., Kyiv 02660, Ukraine 2) Taras Shevchenko National University of Kyiv, 12 Lva Tolstoho St., Kyiv 01033, Ukraine

Faculty of Chemistry, Department of Organic Chemistry

Ph.D. Student

Pavlo O. Iegorov, 1) Enamine Ltd., 78 Chervonotkatska St., Kyiv 02660, Ukraine 2) Taras Shevchenko National University of Kyiv, 12 Lva Tolstoho St., Kyiv 01033, Ukraine

Faculty of Chemistry, Department of Organic Chemistry

Student

Alexey V. Dobrydnev, 1) Enamine Ltd., 78 Chervonotkatska St., Kyiv 02660, Ukraine 2) Taras Shevchenko National University of Kyiv, 12 Lva Tolstoho St., Kyiv 01033, Ukraine

Faculty of Chemistry, Department of Organic Chemistry

Researcher

Yulian M. Volovenko, Taras Shevchenko National University of Kyiv, 12 Lva Tolstoho St., Kyiv 01033, Ukraine

Faculty of Chemistry, Department of Organic Chemistry

Prof. Dr.

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Published

2021-02-23

Issue

Vol. 57 No. 2 (2021)

Section

Original Papers