Related Experiment Video
Updated: Aug 5, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Cobalt-Catalyzed Reductive Asymmetric Dimerization of 1,3-Enynes: Rapid Synthesis of Enantioenriched Skipped
Jia-Ni Lin1, Xing-Fu Wei1, Qiong Yu1
1Shenzhen Grubbs Institute, Department of Chemistry, and Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, Guangdong, People's Republic of China.
Abstract:
Enantioenriched skipped polyenes represent an important building block in natural products and bioactive molecules. Thus, it is of great importance for developing efficient methods for the synthesis of enantioenriched skipped polyenes yet challenging. To date, no example for direct access to skipped polyenes with controlled stereochemistry from simple and readily available starting materials has been developed. Herein, a cobalt-catalyzed reductive asymmetric cross-dimerization of 1,3-enynes has been developed, affording the first rapid access to enantioenriched skipped 1,3,6-trienes from readily available simple starting materials. Moreover, this protocol is amenable to enantioenriched skipped dienes by asymmetric reductive cross-hydrodimerization of 1,3-enynes with alkynes. Mechanistic investigations revealed a domino process by a chemoselective and non-regioselective semi-reduction of 1,3-enynes to 1,3-dienes followed by a chemo-, regio-, and enantioselective cross-hydrodimerization of 1,3-dienes with 1,3-enynes. Notably, asymmetric reductive hydrodimerization of enynes represents the first example of synthesizing enantioenriched 1,3,6-trienes, 1,3,5,8,10-pentaenes, 1,4-dienes from achiral starting materials.
Related Concept Videos
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

