128669-78-3Relevant academic research and scientific papers
New Entry to the Perhydrofurofuran Ring System
Kido, Fusao,Sinha, Subhash C.,Abiko, Toshiya,Watanabe, Masataka,Yoshikoshi, Akira
, p. 418 - 420 (2007/10/02)
Treatment of the α-diazomalonate (6) with Rh2(OAc)4 stereoselectively provided substituted valerolactones (7) and (7') via the sigmatropic rearrangement of a nine-membered cyclic allylsulphonium ylide; the rearrangement product was converted to 5-alk
Stereoselectivity in the sigmatropic rearrangement of eight- and nine-membered cyclic allylsulfonium ylides. Synthesis of vinyl- substituted butyro- and valerolactones
Kido, Fusao,Sinha, Subhash C.,Abiko, Toshiya,Watanabe, Masataka,Yoshikoshi, Akira
, p. 4887 - 4906 (2007/10/02)
The rhodium (II) acetate-catalyzed [2,3]sigma-tropic rearrangement of the diazo malonates of (z)-4-phen-ylthio-2-buten-1-ol derivatives 6 afforded vinyl-substituted butyrolactones 10 in a highly stereoselective manner, while the rearrangement of the diazo malonates of homologues, (z)-5-phenylthio-3-penten-1-ol derivatives 9, yielded vinyl-substituted valerolactones 13 and 14 in the predominance of the formers. A stereochemically fixed substituent R in 9 was found to be an important factor resulting to high stereoselectivity in the latter rearrangement as shown by using diazo malonate 20b as substrate.
