103745-07-9Relevant articles and documents
Enzyme-mediated enantioselective hydrolysis of 1,2-diol monotosylate derivatives bearing an unsaturated substituent
Matsumoto,Oohana,Hashimoto,Usuda,Shimoda,Ohshima,Suzuki,Togawa
, p. 3981 - 3988 (2018/06/15)
We have succeeded in the easy preparation of optically active 1,2-diol monotosylates bearing an unsaturated substituent via enzymatic hydrolysis. Lipase PS quickly catalyzes the hydrolyses of 2-acetoxybut-3-enyl tosylate, which has a double bond, and 2-acetoxybut-3-ynyl tosylate, which has a triple bond, with excellent enantioselectivity to afford the corresponding optically active compounds. The reaction is also applicable to acetates with a longer chain, which has a double bond at the terminus. To demonstrate the applicability of this method, enantiomerically pure (R)-massoialactone, a natural coconut flavor, has been synthesized from racemic 2-acetoxypent-4-enyl tosylate in several steps. Furthermore, the enzyme can recognize the stereochemistry of olefins, and the (Z)-alkenyl structure is more suitable for the enantioselective hydrolysis than the (E)-isomer.
Ring opening of 2,3-epoxy 1-tosylates to halohydrins and subsequent elaboration to asymmetrical alcohols
Federici,Federici, Chiara,Righi,Righi, Giuliana,Rossi,Rossi, Leucio,Bonini,Bonini, Carlo,Chiummiento,Chiummiento, Lucia,Funicello,Funicello, Maria
, p. 797 - 800 (2007/10/02)
2,3-epoxy alcohols-1-tosylates are regio and chemoselectively opened to the corresponding 3-halohydrins (I, Br, Cl): the reduction of the iodohydrins to the monoprotected diols and subsequent standard coupling of the tosyl group leads to a straightforward synthesis of optically active naturally occurring pheromones