75154-95-9Relevant academic research and scientific papers
Thermal -Sigmatropic Hydrogen Shifts: Stereochemistry, Kinetics, Isotope Effects, and ?-Facial Selectivity
Hoeger, Carl A.,Johnston, Allen D.,Okamura, William H.
, p. 4690 - 4698 (2007/10/02)
The antarafacial stereochemistry of the thermal -sigmatropic hydrogen shift has been demonstrated.The substrates studied include the epimeric cis-isotachysterol analogues 1 and 4 and their stereospecifically 15α-deuterium-labelled derivatives 7 and 1
Thermal Rearrangement of Vinylallenes: Synthesis of 3-Deoxy-1α-hydroxy-14-epiprevitamin D3
Jeganathan, S.,Johnston, Allen D.,Kuenzel, Elizabeth A.,Norman, Anthony W.,Okamura, Willian H.
, p. 2152 - 2158 (2007/10/02)
The lithium salt of the terminal allene 12a was reacted with keto enol ether 13 to give the vinylallenones 8a(6R) and 9a(6S).On reduction with sodium borohydride, 8a afforded vinylallenols 8b(1R,6R) and 8c(1S,6R); similarly 9a gave 9b(1R,6S) and 9c(1S,6S)
Studies on Vitamin D (Calciferol) and Its Analogues. 18. The Vinylallene Approach to the 1-Hydroxyvitamin D System. New Sigmatropic Reactions in the Vitamin D Series
Condran, Patrick,Hammond, Milton L.,Mourino, Antonio,Okamura, William H.
, p. 6259 - 6267 (2007/10/02)
The thermally induced -sigmatropic hydrogen shift of the diastereomeric vitamin D type vinylallenols 6a (1R,6R), 6b (1R,6S), 7a (1S,6S) and vinylallenols 5a (6R) and 5b (6S) were studied.The 1S,6S (7b) and 1R,6R(6a) alcohols afforded ca. 60percent yi
