Highly Selective Addition of a Broad Spectrum of Trimethylsilane Pro‐nucleophiles to N‐tert‐Butanesulfinyl Imines |
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| Authors: | Manas Das Prof?Dr Donal F O'Shea |
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| Affiliation: | 1. Department of Pharmaceutical and Medicinal Chemistry, Royal College of Surgeons in Ireland, 123 St. Stephen's Green, Dublin 2 (Ireland);2. School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4 (Ireland). |
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| Abstract: | Addition of organotrimethylsilane reagents to chiral N‐tert‐butanesulfinyl imines can be achieved in good yields and with excellent diastereoselectivities by employing TMSO?/Bu4N+ as a Lewis base activator in THF. A variety of aliphatic, aromatic, heteroaromatic and organometallic chiral imines were utilised as electrophiles for the synthesis of enantioenriched N‐tert‐butanesulfinyl amides. Remarkably, the same sets of reaction conditions could be used with a highly diverse range of bench‐stable organotrimethylsilane reagents, which highlights the generality and robustness of this methodology. |
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| Keywords: | chiral imines diastereoselectivity organotrimethylsilanes pro‐nucleophiles trimethylsilyloxide activation |
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