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Synfacts 2018; 14(11): 1145
DOI: 10.1055/s-0037-1611240
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Hydrothiolation of 1,3-Dienes

Rezensent(en):
Hisashi Yamamoto
,
Takahiro Sawano
Yang X.-H, Davison RT, Dong VM. * University of California-Irvine, USA
Catalytic Hydrothiolation: Regio- and Enantioselective Coupling of Thiols and Dienes.

J. Am. Chem. Soc. 2018;
140: 10443-10446
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Publikationsverlauf

Publikationsdatum:
18. Oktober 2018 (online)

 
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Key words

rhodium catalysis - hydrothiolation - thiols - dienes - sulfides

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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