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

• Mizuta, Satoshi

• Onomura, Osamu

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.

RSC Advances, 2(6), pp.2266-2269; 2012

Journal

• RSC Advances

  RSC Advances 2 (6), 2266-2269, 2012-03-14

  Royal Society of Chemistry

Keywords

• Alkenyl
• Boronic acid
• Diastereoselective additions
• Diastereoselective synthesis
• Nucleophilic additions
• Piperidine rings
• Receptor antagonists
• Stereoselectivity

Details

• CRID: 1050005822298255104
• NII Article ID: 120006985425
• ISSN: 20462069
• DOI: 10.1039/c2ra01254e
• HANDLE: 10069/29073
• Web Site: https://nagasaki-u.repo.nii.ac.jp/records/10551
• Web Site: http://pubs.rsc.org/en/content/articlepdf/2012/RA/C2RA01254E
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • Crossref
  • CiNii Articles
  • KAKEN