Development and application of a new general method for the asymmetric synthesis of syn- and anti-1,3-amino alcohols
摘要：
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.
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关键词：
amino alcohols (acyclic compounds amino alcohols (benzene compounds diastereoselective syntheses, enantioselective syntheses (incl. cis/trans‐isomerism alkaloids
DOI：
10.1002/chin.200401065
被引量：
年份：
2003
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