- Bi(OTf)3 catalyzed synthesis of acyclic β-sulfanyl ketones via a tandem Meyer-Schuster rearrangement/conjugate addition reaction
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A new strategy to prepare acyclic β-carbonyl thioethers from propargyl alcohols and sulfur nucleophiles is reported. The investigation of the reaction substrates scope indicated that primary 3-aryl propargyl alcohols and thiols underwent the transformation smoothly. The reaction probably proceeded a Bi(OTf)3-catalyzed tandem Meyer-Schuster rearrangement of 3-aryl propargyl alcohol, followed by a thiol Michael conjugate addition of thiols to in situ generated α, β-unsaturated ketones. The method was 100% atom economic, high-yielding, and easy to handle, making it a valuable method for the construction of β-carbonyl sulfides.
- Wang, Yuan,Yin, Yan,Zhang, Qinglin,Pan, Wanyong,Guo, Huifeng,Pei, Keke
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supporting information
p. 2030 - 2034
(2019/07/03)
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- 1,4-Asymmetric reduction of γ-keto sulfoxides bearing the 2,4,6-triisopropylphenyl group
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Reduction of γ-keto sulfoxides bearing the 2,4,6-triisopropylphenyl group with DIBAL gives γ-hydroxy sulfoxides with high stereoselectivity in the ratio 95:5. In comparison with the lower stereoselectivities obtained in the reaction of γ-keto sulfoxides bearing p-tolyl or 2,4,6-trimethylphenyl groups, the sterically bulky (2,4,6-triisopropylphenyl)-sulfinyl group is extremely efficient in effecting high 1,4-remote asymmetric induction. The Royal Society of Chemistry 2000.
- Nakamura, Shuichi,Kuroyanagi, Masayuki,Watanabe, Yoshihiko,Toru, Takeshi
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p. 3143 - 3148
(2007/10/03)
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