68330-44-9Relevant academic research and scientific papers
Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C-O Bond Activation
Magre, Marc,Paffenholz, Eva,Maity, Bholanath,Cavallo, Luigi,Rueping, Magnus
supporting information, p. 14286 - 14294 (2020/09/15)
A magnesium-catalyzed regiodivergent C-O bond cleavage protocol is presented. Readily available magnesium catalysts achieve the selective hydroboration of a wide range of epoxides and oxetanes yielding secondary and tertiary alcohols in excellent yields and regioselectivities. Experimental mechanistic investigations and DFT calculations provide insight into the unexpected regiodivergence and explain the different mechanisms of the C-O bond activation and product formation.
Biosynthesis of the off-flavor 2-methylisoborneol by the myxobacterium Nannocystis exedens
Dickschat, Jeroen S.,Nawrath, Thorben,Thiel, Verena,Kunze, Brigitte,Mueller, Rolf,Schulz, Stefan
, p. 8287 - 8290 (2008/09/18)
(Chemical Equation Presented) A bouquet of bacteria: Methylisoborneol (1) is a widely occurring volatile from bacteria and an undesirable flavor (off-flavor) in the food industry. The analysis of isotopomers obtained by feeding isotopically labeled precursors to myxobacteria revealed the biosynthetic pathway to 1. Geranylpyrophosphate (CPP) is alkylated by S-adenosylmethionine (SAM) and the product is cyclized to 1. The methylation of GPP is unprecedented in nature.
Synthesis of 2,2,-Disubstituted Oxetanes from Ketones with S-Methyl-S-(sodiomethyl)-N-(4-tolylsulfonyl)sulfoximine
Welch, Steven C.,Rao, A. S. C. Prakasa,Lyon, John T.,Assercq, Jean-Marie
, p. 252 - 257 (2007/10/02)
A covenient and facile one-step synthesis of 2,2-disubstituted oxetanes from ketones utilizing S-methyl-S-(sodiomethyl)-N-(4-tolylsulfonyl)sulfoxymine in dimethyl sulfoxide is presented.The stereochemistry and chemical reactivity of some 2,2-disubstituted
