191422-46-5Relevant academic research and scientific papers
Extremely Efficient Chiral Induction in Conjugate Additions of p-Tolyl α-Lithio-β-(trimethylsilyl)ethyl Sulfoxide and Subsequent Electrophilic Trapping Reactions
Nakamura, Shuichi,Watanabe, Yoshihiko,Toru, Takeshi
, p. 1758 - 1766 (2007/10/03)
Reaction of p-tolyl α-lithio-β-(trimethylsilyl)ethyl sulfoxide with α,β-unsaturated esters gave the conjugate addition products as a single diastereomer. The intermediate enolates were subsequently trapped with various alkyl halides or aldehydes to give the products with extremely high stereoselectivity. The reaction with α,β-unsaturated ketones also proceeded with high diastereoselectivity. Protolysis of the enolates derived from the α-methyl-α,β-unsaturated esters gave the products with high stereoselectivity. The stereo- and regioselective elimination of the sulfinyl group gave chiral homoallylic carboxylates.
Stereoselective conjugate addition of an α-sulfinyl carbanion to α,β-unsaturated esters: Asymmetric synthesis of cycloalkanecarboxylates
Toru, Takeshi,Nakamura, Shuichi,Takemoto, Hirofumi,Ueno, Yoshio
, p. 449 - 450 (2007/10/03)
The reaction of lithiated (R)-2-(trimethylsilyl)ethyl p-tolyl sulfoxide 1 with α,β-unsaturated esters gives 1,4-conjugate addition products as single stereoisomers, whereas the reaction of 1 with 4-, 6-, or 7-haloalkenoates affords cyclopropane-, cyclopen
