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Z-Stereoselective Aza-Peterson Olefinations with Bis(trimethylsilane) Reagents and Sulfinyl Imines

Manas Das and Donal F. O’Shea*

*Department of Pharmaceutical and Medicinal Chemistry, Royal College of Surgeons in Ireland, 123 St. Stephen’s Green, Dublin 2, Ireland, Email: donalfoshearcsi.ie

M. Das, D. F. O'Shea, Org. Lett., 2016, 18, 336-339.

DOI: 10.1021/acs.orglett.5b03519 (free Supporting Information)


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Abstract

The use of TMSO-/Bu4N+ as Lewis base activator enables highly stereoselective aza-Peterson olefinations from bench-stable α,α-bis(trimethylsilyl)toluene reagents and N-substituted imines. N-t-butanesulfinyl imines were utilized for the synthesis of Z-stilbenes with excellent selectivities, while N-aryl imines generated E-stilbenes under identical reaction conditions via syn-elimination of an in situ formed hypervalent silicate.

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Key Words

Peterson Olefination, anti-elimination, syn-elimination


ID: J54-Y2016