Chemodivergent Multicomponent Reactions of Morita–Baylis–Hillman-Type Yne-allylic Esters with 1,3-Dicarbonyls or Aroylacetonitriles
Herein, we introduce Morita-Baylis-Hillman-type yne-allylic esters that serve as novel precursors in a chemodivergent multicomponent reaction platform with carbon-based nucleophiles. S<sub><i>N</i></sub>2″ addition of tertiary amines generates unprecedented vinyl-allenyl ammonium intermediates, whose reactivity is substrate controlled. 1,3-Dicarbonyls afford linear dienol esters via an ABC-type multicomponent reaction (MCR), while aroylacetonitriles trigger a tandem [5 + 1] annulation to give bicyclic lactols. This work provides both a new MCR for drug conjugate synthesis and an efficient route to natural product-like bicyclic lactol scaffolds.
Authors
- Chao-Xu Li
- Hua Xiao (ORCID: https://orcid.org/0000-0001-6100-0969)
- Chong-Ming Dai
- Xiaojing Ma
- Huixia Zhu (ORCID: https://orcid.org/0000-0001-7216-9735)
- Chen Huang
- Fu-Fang Wu
- Huai Wang
- Guang-Jie Wang
Institutions
- Fuyang Normal University (CN)
- Hefei University of Technology (CN)
- Biomass Technology Group (Netherlands) (NL)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-02-26
- DOI
- https://doi.org/10.1021/acs.orglett.6c00211
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00