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

被引：172

作者：

Kochi, T ^{[1
]}

Tang, TP ^{[1
]}

Ellman, JA ^{[1
]}

机构：

[1] Univ Calif Berkeley, Ctr New Direct Organ Synth, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 37期

关键词：

D O I：

10.1021/ja0363462

中图分类号：

O6 [化学];

学科分类号：

0703 ;

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 LiBHEt3 provides syn- and ant 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.

引用

页码：11276 / 11282

页数：7

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