167611-58-7Relevant academic research and scientific papers
Enantioselective synthesis of both (+)-and (-)-derivatives of bicyclo[4.3.0]nonan-8-one and -3,8-diones from R-carvone 1
Srikrishna, Adusumilli,Reddy, T. Jagadeeswar,Nagaraju, Sankuratri
, p. 1679 - 1682 (1996)
Enantioselective synthesis of both the enantiomeric forms of the hydrindane derivatives mentioned in the title, potential chiral precursors in terpenoid synthesis, starting from R-carvone employing two different cyclopentannulation methodologies is described.
Application of Microwave Heating Technique for Rapid Synthesis of γ,δ-Unsaturated Esters
Srikrishna, Adusumilli,Nagaraju, Sankuratri,Kondaiah, Paturu
, p. 1809 - 1816 (2007/10/02)
The use of microwave heating technique for the acceleration of ortho ester Claisen rearrangement (a three step transformation) is described.Irradiation of a DMF solution of the allyl alcohol 5, triethyl orthoacetate and propionic acid (catalytic) in an Erlenmeyer flask for 10 minutes in a microwave oven generated the ester 8 in 83percent yield.Analogously, ortho ester Claisen rearrangement of a variety of allyl and propargyl alcohols (9, 12-22) were achieved.The formation of the diester 10 from 2-butyne-1,4-diol (9) via the ortho ester Claisen rearrangement of two allyl alcohol moieties (involving six steps) in 15 minutes, demonstrates the versatility of the microwave heating technique.
The claisen rearrangement in synthesis: Acceleration of the johnson orthoester protocol en route to bicyclic lactones
Jones, Graham B.,Huber, Robert S.,Chau, Sotheary
, p. 369 - 380 (2007/10/02)
Catalysis of the Claisen orthoester rearrangement of triethyl orthoacetate and a number of 2-cycloalken-1-ols has been achieved using acidic catalysis and brief microwave thermolysis in DMF. Unlike conventional methods of thermolysis, very high yields of rearranged products are typically obtained in less than ten minutes, and the Claisen products themselves require no further purification. The synthetic utility of the products so obtained is demonstrated in a general synthesis of functionalized bicyclic lactones.
