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Updated: Jun 20, 2026

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Published on: May 26, 2019
Tunable and highly regio- and diastereoselective vinylogous Mannich-type reaction of dioxinone-derived silyl
Chun-Ling Gu1, Li Liu, Dong Wang
1Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Abstract:
A tunable and highly regio- and diastereoselective vinylogous Mannich-type reaction of dioxinone-derived silyl dienolate (1) with chiral N-tert-butanesulfinyl imino ester (2) was developed. By appropriate choice of Lewis acid catalyst, two diastereomers of the gamma-product were obtained, respectively, with dr up to 95:5. The procedure for the Ag(I)-catalyzed vinylogous Mannich-type reaction also provided facile access to the alpha-regioisomer with excellent diastereoselectivities (up to >99:1 dr) by changing the counterion of the Ag(I) salt.
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