- A convenient enantioselective CBS-reduction of arylketones in flow-microreactor systems
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A convenient, versatile, and green CBS-asymmetric reduction of aryl and heteroaryl ketones has been developed by using the microreactor technology. The study demonstrates that it is possible to handle borane solution safely within microreactors and that the reaction performs well using 2-MeTHF as a greener solvent.
- De Angelis, Sonia,De Renzo, Maddalena,Carlucci, Claudia,Degennaro, Leonardo,Luisi, Renzo
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supporting information
p. 4304 - 4311
(2016/05/24)
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- Regio- and stereoselective ring opening of enantiomerically enriched 2-aryl oxetanes and 2-aryl azetidines with aryl borates
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(Chemical Equation Presented) The regioselective ring opening of 2-aryl-substituted four-membered heterocyclic rings with phenols, including catechol, was achieved by the use of aryl borates in mild and neutral reaction conditions without the aid of any transition metal catalysts. While β-alkyl azetidines were found not to be reactive, optically active N-tosyl azetidines gave the corresponding β-aryloxy amines in a racemic form, thus indicating the considerable carbocationic character of the transition state. The introduction of a hydroxyl group in the azetidine ring (i.e., an azetidinol), able to anchor the aryl borate and to direct the subsequent nucleophilic delivery, was shown to determine the ring-opening process with predominant inversion of configuration. When enantiomerically enriched 2-aryl oxetanes were used, the reduced extent of racemization observed (up to 93:7 er) was rationalized by an intramolecular delivery through a six-membered transition state, giving β-aryloxy alcohols with a predominant retention of configuration (i.e., a syn-stereoselective ring opening). The aryloxy alcohols obtained, endowed with suitable functionalities, can be cyclized to give access to enantiomerically enriched 2-aryl-1,5-benzodioxepins.
- Bertolini, Ferruccio,Crotti, Stefano,Di Bussolo, Valeria,Macchia, Franco,Pineschi, Mauro
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supporting information; experimental part
p. 8998 - 9007
(2009/04/11)
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- N-phenyl-N′-phenylpopylpiperazine derivatives and process for the preparation
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The present invention is directed to an N-phenyl-N′-phenylpropylpiperazine derivative represented by formula (1): (wherein R1represents a lower alkyl group; R2represents a lower alkoxy group; and R3represents a cyano group
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- Indole derivative for treating overproduction of dihydrotestosterone
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The present invention relates to an indole derivative represented by formula (1) or a salt thereof, and a pharmaceutical containing the derivative or the salt: STR1 wherein R 1 represents lower alkyl; R 2 represents hydrogen or phenyl which may be substit
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