123387-51-9Relevant articles and documents
Total synthesis of tropinone using 1,3-dipolar cycloaddition of cyclic azomethine ylide and phenyl vinyl sulfone as the key step
Laha, Joydev K.
, p. 254 - 256 (2010)
Total synthesis of tropinone from the readily available piperidone 2 is described. The rapid assembly of the tropane skeleton was achieved by 1,3-dipolar cycloaddition of cyclic azomethine ylide 3 to phenyl vinyl sulfone.
High-Temperature Boc Deprotection in Flow and Its Application in Multistep Reaction Sequences
Bogdan, Andrew R.,Charaschanya, Manwika,Dombrowski, Amanda W.,Wang, Ying,Djuric, Stevan W.
supporting information, p. 1732 - 1735 (2016/05/19)
A simplified Boc deprotection using a high-temperature flow reactor is described. The system afforded the qualitative yield of a wide variety of deprotected substrates within minutes using acetonitrile as the solvent and without the use of acidic conditions or additional workups. Highly efficient, multistep reaction sequences in flow are also demonstrated wherein no extraction or isolation was required between steps.
Driving an equilibrium acetalization to completion in the presence of water
Minakawa, Maki,Yamada, Yoichi M. A.,Uozumi, Yasuhiro
, p. 36864 - 36867 (2014/11/08)
Formation of an acetal from a carbonyl substrate by condensation with an alcohol is a classical reversible equilibrium reaction in which the water formed must be removed to drive the reaction to completion. A new method has been developed for acetalization of carbonyl substrates by diols in the presence of water. Complexation of poly(4-styrenesulfonic acid) with poly(4-vinylpyridine) generates a catalytic membrane of polymeric acid at the interface between two parallel laminar flows in a microchannel of a microflow reactor. The catalytic membrane provides a permeable barrier between the organic layer and water-containing layer in the reaction, and permits discharge of water to the outlet of the microreactor to complete the acetalization. Condensation of a variety of carbonyl substrates with diols proceeded in the presence of water in the microflow device to give the corresponding acetals in yields of up to 97% for residence times of 19 to 38 s. the Partner Organisations 2014.
