142188-53-2Relevant academic research and scientific papers
Hypervalent iodine(III) catalyzed radical hydroacylation of chiral alkylidenemalonates with aliphatic aldehydes under photolysis
Selvakumar, Sermadurai,Kang, Qi-Kai,Arumugam, Natarajan,Almansour, Abdulrahman I.,Kumar, Raju Suresh,Maruoka, Keiji
, p. 5841 - 5846 (2017/09/09)
Hypervalent iodine(III) catalyzed diastereoselective radical hydroacylation of alkylidenemalonates bearing (?)-8-phenylmenthol as a chiral auxiliary with aliphatic aldehydes is realized under photolysis. This work represent the first example of diastereoselective addition of acyl radicals to olefins to afford chiral ketones in a highly stereoselective fashion. The reaction is initiated by the photolysis of hypervalent iodine(III) catalyst under mild and metal-free conditions. The synthetic potential of this methodology was demonstrated by the short formal synthesis of (?)-methyleneolactocin.
Diastereoselective Radical Hydroacylation of Alkylidenemalonates with Aliphatic Aldehydes Initiated by Photolysis of Hypervalent Iodine(III) Reagents
Selvakumar, Sermadurai,Sakamoto, Ryu,Maruoka, Keiji
supporting information, p. 6552 - 6555 (2016/05/09)
Diastereoselective radical hydroacylation of chiral alkylidenemalonates with aliphatic aldehydes is realized by the combination of a hypervalent iodine(III) reagent and UV-light irradiation. The reaction is initiated by the photolysis of hypervalent iodine(III) reagents under mild, metal-free conditions, and is the first example of diastereoselective addition of acyl radicals to olefins to afford chiral ketones in a highly stereoselective fashion. The obtained optically active ketones are useful chiral synthons, as exemplified by the short formal synthesis of (-)-methyleneolactocin.
An enantioselective synthesis of 3,4-disubstituted butyrolactones
Honda,Kimura
, p. 77 - 78 (2007/10/02)
An enantioselective synthesis of γ-butyrolactones including a formal synthesis of (-)-methylenolactocin 1 is achieved by employing an enantioselective deprotonation of 3-phenylcyclobutanone as a key step.
Novel, Enantioselective Lactone Construction. First Synthesis of Methylenolactocin, Antitumor Antibiotic from Penicillium sp.
Azevedo, Mariangela B. M. de,Murta, Maria M.,Greene, Andrew E.
, p. 4567 - 4569 (2007/10/02)
The first synthesis of (-)-methylenolactocin, which illustrates a novel approach to enantiopure γ-butyrolactones and serves to confirm the structure and establish the absolute stereochemistry of the natural product, is reported.
