19780-84-8Relevant articles and documents
Generation of α,β-unsaturated platinum carbenes from homopropargylic alcohols: Rearrangements to polysubstituted furans
Allegretti, Paul A.,Ferreira, Eric M.
supporting information; experimental part, p. 5924 - 5927 (2011/12/16)
A number of diversely substituted furans are synthesized via a cycloisomerization process that goes through a unique metal carbene species. Both ligand structure and the nature of the leaving group are evaluated. The characteristics of the carbene intermediate can be modulated, resulting in highly selective hydrogen or silicon group migrations.
Organoboranes for Synthesis. 15. B-Allenyl-9-BBN: A Highly Regiospecific and Chemoselective Reagent for Allenylboration of Representative Carbonyl Compounds, Leading to Homopropargylic Alcohols and Amines
Brown, Herbert C.,Khire, Uday R.,Narla, Gowriswari,Racherla, Uday S.
, p. 544 - 549 (2007/10/02)
Reactions of B-allenyl-9-BBN (11) with representative carbonyl compounds, such as aldehydes, ketones, acid chlorides, carboxylic acid esters, and imines, proceed cleanly with the allenyl moiety undergoing transfer to the carbonyl or imine carbon, with allenic to propargylic rearrangement, and the boron moiety to the carbonyl oxygen or imine nitrogen.A simple oxidation with alkaline hydrogen peroxide results in the formation of the corresponding homopropargylic alcohols and amines in excellent yields.Aldehydes, ketones, and imines react in a 1:1 stoichiometry, while acid chlorides and carboxylic acid esters react with 2 equiv of the reagent.The relative reactivities of representative aldehydes, ketones, and esters toward 11 were also explored.Besides being highly regiospecific, the reagent 11 also possesses a remarkable chemoselectivity.B-Allenyl-9-BBN can distinguish between less and more sterically hindered aldehydes, ketones, and esters, making possible the clean and selective propargylboration of a desired carbonyl group in complex organic molecules containing less reactive functional groups.
SYNTHESIS OF HEPIALONE, A SEX-PHEROMONE OF HEPIALUS CALIFORNICUS B
Yadav, J S,Rao, E Sreenivasa
, p. 2315 - 2324 (2007/10/02)
A simple synthesis of (+/-)-hepialone, a sex pheromone of Hepialus californicus B is reported by employing a 1,3-dipolar cycloaddition as a key step.
