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

Contributor(s):
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
Further Information

Publication History

Publication Date:
18 October 2018 (online)

 

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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