Development and application of a new general method for the asymmetric synthesis of syn- and anti-1,3-amino alcohols

Takuya Kochi, Tony P. Tang, Jonathan A. Ellman

Research output: Contribution to journalArticle

148 Citations (Scopus)

Abstract

A general method is described for asymmetric synthesis of both syn- and anti-1,3-amino alcohols. The first application of metalloenamines derived from N-sulfinyl imines is reported for the highly diastereoselective addition to aldehydes. The reduction of the product β-hydroxy N-sulfinyl imines 2 with catecholborane and LiBHEt3 provides syn- and anti-1,3-amino alcohols with very high diastereomeric ratios. This method was found to be effective for a variety of substrates incorporating either aromatic or various aliphatic substituents. The convergent and efficient asymmetric syntheses of the two natural products, (-)-8-epihalosaline and (-)-halosaline, were also accomplished.

Original languageEnglish
Pages (from-to)11276-11282
Number of pages7
JournalJournal of the American Chemical Society
Volume125
Issue number37
DOIs
Publication statusPublished - 2003 Sep 17
Externally publishedYes

ASJC Scopus subject areas

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

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