Catalytic enantioselective synthesis of α-aminooxy and α-hydroxy ketone using nitrosobenzene

Norie Momiyama, Hisashi Yamamoto

Research output: Contribution to journalArticle

220 Citations (Scopus)

Abstract

The highly enantioselective and O-selective nitroso aldol reaction of tin enolates 2 and nitrosobenzene (1) has been developed with the use of (R)-BINAP-silver complexes as a catalyst. After the various silver salts were surveyed, the AgOTf and the AgClO4 complex were found to be optimal in the O-selective nitroso aldol reaction in both asymmetric induction (up to 97% ee) and regioselection (O/N = >99/1), affording aminooxy ketone 3. The product 3 can be transformed to α-hydroxy ketone 5 without any loss of enantioselectivity. Thus, the method provides an efficient approach to the catalytic enantioselective introduction of oxygen α- to the carbonyl group.

Original languageEnglish
Pages (from-to)6038-6039
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number20
DOIs
Publication statusPublished - 2003 May 21

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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