606954-72-7Relevant academic research and scientific papers
Development and application of a new general method for the asymmetric synthesis of syn- and anti-1,3-amino alcohols
Kochi, Takuya,Tang, Tony P.,Ellman, Jonathan A.
, p. 11276 - 11282 (2003)
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.
