FUNCTIONALIZATION OF FOUR-MEMBERED CYCLIC SULFOXIMINES BY A CONVENIENT LITHIATION/TRAPPING SEQUENCE

Авторы

  • Arianna Tota Department of Pharmacy – Drug Sciences, University of Bari Aldo Moro, Via E. Orabona 4, Bari 70125
  • Flavio Fanelli CNR, Institute of Crystallography IC-CNR, Via Amendola 127/A, Bari 70125
  • Aurelia Falcicchio CNR, Institute of Crystallography IC-CNR, Via Amendola 127/A, Bari 70125
  • Renzo Luisi Department of Pharmacy – Drug Sciences, University of Bari Aldo Moro, Via E. Orabona 4, Bari 70125
  • Leonardo DEGENNARO Department of Pharmacy – Drug Sciences, University of Bari Aldo Moro, Via E. Orabona 4, Bari 70125

DOI:

https://doi.org/10.1007/3675

Ключевые слова:

cyclic sulfoximines, four-membered heterocycles, lithiation, stereoselectivity, N-transfer

Аннотация

The functionalization of four-membered cyclic sulfoximine, based on a lithiation/electrophile trapping sequence, led to unprecedented C(2)-substituted N-Boc-1-imino-1-imino-1λ6-thietane 1-oxide in moderate to good yields. Interestingly, the reaction proceeded with high stereocontrol showing a preferential bias for an introduction of the electrophile syn to the oxygen on the sulfur. Starting from thietan-1-one, by a combination of lithiation/electrophile trapping followed by N-transfer, it is possible to obtain the stereoisomer bearing the electrophile syn to the nitrogen on the sulfur. Thus, all stereoisomers can be accessible for medicinal chemistry studies.

Биографии авторов

Arianna Tota, Department of Pharmacy – Drug Sciences, University of Bari Aldo Moro, Via E. Orabona 4, Bari 70125

Ph.D. student, Department of pharmacy-drug sciences

Flavio Fanelli, CNR, Institute of Crystallography IC-CNR, Via Amendola 127/A, Bari 70125

Ph.D. student, CNR, Institute of Crystallography IC-CNR

Aurelia Falcicchio, CNR, Institute of Crystallography IC-CNR, Via Amendola 127/A, Bari 70125

Post-Doctorate, CNR, Institute of Crystallography IC-CNR

Renzo Luisi, Department of Pharmacy – Drug Sciences, University of Bari Aldo Moro, Via E. Orabona 4, Bari 70125

Associate professor, Department of pharmacy-drug sciences

Leonardo DEGENNARO, Department of Pharmacy – Drug Sciences, University of Bari Aldo Moro, Via E. Orabona 4, Bari 70125

Assistant professor, Department of pharmacy-drug sciences

Загрузки

Опубликован

2017-04-18

Выпуск

Том 53 № 3 (2017): Предпочтительные гетероциклические структуры в химической биологии и разработке лекарств: синтез и биоактивность

Раздел

Оригинальные статьи