196600-07-4Relevant academic research and scientific papers
Anodic oxidation: An attractive alternative to CAN-mediated cleavage of para-methoxyphenyl ethers
Vaxelaire, Carine,Souquet, Florence,Lannou, Marie-Isabelle,Ardisson, Janick,Royer, Jacques
supporting information; experimental part, p. 3138 - 3140 (2009/12/05)
para-Methoxyphenyl (PMP) ether is a very convenient protecting group for the alcohol function; however, its cleavage requires strong oxidative conditions. In this field, the use of powerful eerie ammonium nitrate has been widely described, despite the fac
Enantioselective synthesis of chromans for the preparation of enantiopure vitamin E and analogues
Tietze, Lutz F.,G?rlitzer, Jochen
, p. 877 - 885 (2007/10/03)
Coupling of the differently protected (hydroxymethyl)enynes 11 a-e and 12a-c with the iodoarene 7 in the presence of catalytic amounts of Pd(PPh3)4 afforded the arylenynes 5a-e and 6a-c which were transformed into the monoprotected chiral trihydroxy compounds 13 a-d and 14a,b by Sharpless bishydroxylation with >95% ee for 13 a-d, 91% ee for 14b, and 64% ee for 14a. A 5-step transformation of 13a led to the desired chroman derivative 3a which was cleaved to give the aldehyde 2 a known precursor for the enantioselective synthesis of vitamin E.
