Chemodivergent Multicomponent Reactions of Morita–Baylis–Hillman-Type Yne-allylic Esters with 1,3-Dicarbonyls or Aroylacetonitriles

Organic Letters 2026

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Authors: Chen Huang, Chao-Xu Li, Guang-Jie Wang, Chong-Ming Dai, Huai Wang, Fu-Fang Wu, Xiaojing Ma, Huixia Zhu, Hua Xiao
DOI: 10.1021/acs.orglett.6c00211
Cited by: 1
References: 28

Abstract

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 N 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.

Fields of Study & Subjects

Catalytic Alkyne Reactions Synthesis of heterocyclic compounds Asymmetric Synthesis and Catalysis

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
10
Pages
3202–3207
Publication date
26 February 2026
Language
EN