- An enantioselective approach to the preparation of chiral sulfones by ir-catalyzed asymmetric hydrogenation
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Several chiral sulfonyl compounds were prepared using the iridium catalyzed asymmetric hydrogenation reaction. Vinylic, allylic and homoallylic sulfone substitutions were investigated, and high enantioselectivity is maintained regardless of the location of the olefin with respect to the sulfone. Impressive stereoselectivity was obtained for dialkyl substitutions, which typically are challenging substrates in the hydrogenation. As expected, the more bulky Z-substrates were hydrogenated slower than the corresponding E isomers, and in slightly lower enantioselectivity.
- Peters, Byron K.,Zhou, Taigang,Rujirawanich, Janjira,Cadu, Alban,Singh, Thishana,Rabten, Wangchuk,Kerdphon, Sutthichat,Andersson, Pher G.
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supporting information
p. 16557 - 16562
(2015/01/09)
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- Catalytic enantioselective reduction of β,β-disubstituted vinyl phenyl sulfones by using bisphosphine monoxide ligands
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(Chemical Equation Presented) Synthesis of chiral sulfones: A copper-phosphine complex efficiently provided optically active alkyl phenyl sulfones by hydrosilylation at room temperature. The reduction of β,β-disubstituted vinyl sulfones in the presence of the Me-DuPhos monoxide ligand lead to excellent enantiomeric excesses and high yields (see scheme). The prepared chiral sulfones were desulfonylated and subjected to Julia olefination conditions.
- Desrosiers, Jean-Nicolas,Charette, Andre B.
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p. 5955 - 5957
(2008/09/17)
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- HETEROCONJUGATE ADDITION OF LITHIUM ALKYLS TO SUBSTITUTED HETERO-OLEFINS CONJUGATED WITH SULFUR AND SILICON ATOMS
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Lithium alkyls and a lithiated sulfone carbanion readily added to the substituted hetero-olefins conjugated with silicon and sulfone-sulfur atoms among other combination of the third (or fourth) row hetero atoms, e.g.Si, Se and S.
- Isobe, Minoru,Kitamura, Masato,Goto, Toshio
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p. 331 - 334
(2007/10/02)
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