title: Development and application of a new general method for the asymmetric synthesis of syn- and anti-1,3-amino alcohols.
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 beta-hydroxy N-sulfinyl imines 2 with catecholborane and LiBHEt(3) 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.
authors.affiliation: Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720, USA.
authors.forename: Takuya
authors.initials: T
authors.lastname: Kochi
authors.forename: Tony P
authors.initials: TP
authors.lastname: Tang
authors.forename: Jonathan A
authors.initials: JA
authors.lastname: Ellman