A stereoselective intramolecular Tsuji-Trost cascade cyclization of (homo)allylic vicinal diacetates with a pendant β-ketoamide or related carbon nucleophile to give γ-lactam-fused vinylcyclopropanes is reported. In addition to two new rings, the products contain three new C-C stereocenters (two of which are quaternary) with a 9:1 dr. Moreover, the reaction proceeds in >94% enantiospecificity with optically enriched starting materials, using an inexpensive carbohydrate as the source of chirality.
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|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6218879 | PMC |
| http://dx.doi.org/10.1021/acs.orglett.8b02232 | DOI Listing |
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