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Diastereoselective addition to N-acyliminium ions with aryl- and alkenyl boronic acids via a Petasis-type reaction


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Title: Diastereoselective addition to N-acyliminium ions with aryl- and alkenyl boronic acids via a Petasis-type reaction
Authors: Mizuta, Satoshi / Onomura, Osamu
Issue Date: 14-Mar-2012
Publisher: Royal Society of Chemistry
Citation: RSC Advances, 2(6), pp.2266-2269; 2012
Abstract: A highly diastereoselective synthesis of 2,3-disubstituted piperidines has been accomplished through nucleophilic additions to N-acyliminium ions with aryl- and alkenyl boronic acids. A reversal of stereoselectivity depending on a β-substituent on the piperidine ring was observed in the alkenylation reactions with (E)-styrylboronic acid. Our strategy was applied in the key step for the synthesis of the neurokinin NK1 receptor antagonist (±)-L-733, 060.
Keywords: Alkenyl / Boronic acid / Diastereoselective additions / Diastereoselective synthesis / Nucleophilic additions / Piperidine rings / Receptor antagonists / Stereoselectivity
URI: http://hdl.handle.net/10069/29073
DOI: 10.1039/c2ra01254e
Rights: © 2012 The Royal Society of Chemistry.
Type: Journal Article
Text Version: author
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/29073

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