52418-89-0Relevant academic research and scientific papers
Novel synthetic approach to (S)-coriolic acid
Babudri, Francesco,Fiandanese, Vito,Marchese, Giuseppe,Punzi, Angela
, p. 327 - 331 (2007/10/03)
A new synthetic approach to (S)-coriolic acid 1 has been developed, starting from the readily available (E)-1-bromo-2-trimethylsilylethene 4 and trimethylsilylacetylene 5. A simple acylation reaction of 4, followed by a coupling reaction of the halogenoderivative intermediate with 5 in the presence of a Pd(0) catalyst affords the monosilylated ketoenyne 7. After desilylation of 7, enantioselective reduction of the carbonyl group with (S)- BINAL-H leads to the alcohol 2 (e.e.=94%). A subsequent coupling reaction and stereoselective reduction of the triple bond affords the target molecule 1.
Stereoselective Conjugate Addition of Halide Anion to Acetylenic Carbonyl Compounds Promoted by Lanthanoid Reagents
Fujisawa, Tamotsu,Tanaka, Akihito,Ukaji, Yutaka
, p. 1255 - 1256 (2007/10/02)
The conjugate addition of halide anion to acetylenic ketones proceeded by the combined use of cerium salts, halotrimethylsilanes and sodium or tetrabutylammonium salts to afford trans-β-halo enones stereoselectively.On the other hand, N,N-diethyl cis-β-haloacrylamides were synthesized from propiolamide.
β-HALOVINYL KETONES: SYNTHESIS FROM ACETYLENIC KETONES
Taniguchi, Mikio,Kobayashi, Shozo,Nakagawa, Masako,Hino, Tohru,Kishi, Yoshito
, p. 4763 - 4766 (2007/10/02)
The reaction of terminal acetylenic ketones with NaI or LiBr gave almost exclusively E-β-iodo-or E-β-bromovinyl ketones in trifluoracetic acid, while Z-β-iodo or Z-β-bromovinyl ketones were the major products in acetic acid.Trimethylsilyl iodide and bromide reacted smoothly with acetylenic ketones at -78 deg C to give TMS-allenolates which were readily converted to β-iodo and β-bromovinyl ketones, respectively.
