106(P-28) キラルな1,2-ジアミンを用いるアルコール類の触媒的不斉アシル化(ポスター発表の部)
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概要
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Asymmetric acylation of alcohols such as racemic alcohols and meso-diols has been widely used to construct various chiral building blocks in the synthesis of biologically active products. Most methods reported so far employed enzymes such as lipase or esterase, but substrate generality is not extensive. We have recently reported a highly enantioselective catalytic asymmetric acylation of racemic secondary alcohols by using a chiral 1,2-diamine derived from (S)-proline (Scheme 1). Furthermore, racemic secondary β-halohydrins were also acylated in high enantioselectivities (Scheme 2). Next, we applied this asymmetric acylation to kinetic resolution of glycerol derivatives. This reaction also proceeded smoothly with high enantioselectivities and gave the corresponding ester and the unreacted alcohol having the opposite absolute configuration each other (Table 1). Additionally, we wish to demonstrate a highly enantioselective catalytic asymmetric acylation of meso-diols using a same chiral 1,2-diamine. This asymmetric acylation of cis-2-cyclopentene-1,4-diol gave the corresponding monoester in excellent enantioselectivities (Scheme 3). Similarly, meso-1,3-, and 1,4-diols were also acylated in high to excellent optical yields (Table 2 and 3). These acylated products were converted to useful chiral building blocks. In conclusion, racemic alcohols and meso-diols can be acylated in excellent enantioselectivitieis using a catalytic amount of a chiral 1,2-diamine. This asymmetric acylation of alcohols has the following distinct advantages; 1) chiral diamine can be readily prepared and handled, 2) high efficiency and excellent enantioselectivities, 3) extensive substrate generality, 4) no metal was used in this reaction, and 5) the acylated products were directly converted to useful chiral building blocks.
- 天然有機化合物討論会の論文
- 2000-10-01
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関連論文
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