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Synfacts 2018; 14(11): 1145
DOI: 10.1055/s-0037-1611240
DOI: 10.1055/s-0037-1611240
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Rhodium-Catalyzed Hydrothiolation of 1,3-Dienes
Further Information
Publication History
Publication Date:
18 October 2018 (online)
![](https://www.thieme-connect.de/media/synfacts/201811/i_h124_s1_10-1055_s-0037-1611240.gif)
Significance
The development of reactions for the construction of C–S bonds is important because molecules essential to life contain this linkage. The addition of thiols to alkenes is a direct and atom-economical method for the formation of C–S bonds. The authors have developed an enantioselective addition of thiols to 1,3-dienes catalyzed by a rhodium–chiral bisphosphine ligand complex to give chiral secondary or tertiary allylic sulfides in good to high enantioselectivities.
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Comment
The enantioselective hydrothiolation proceeds selectively at the more-substituted double bond. A broad range of functional groups are tolerated in this reaction, and the catalyst loading can be lowered to 0.1 mol%.
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![](https://www.thieme-connect.de/media/synfacts/201811/i_h124_s1_10-1055_s-0037-1611240.gif)