posted on 2003-08-23, 00:00authored byTakuya Kochi, Tony P. Tang, Jonathan A. Ellman
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.