Organocatalytic entry to chiral bicyclo[3.n.1]alkanones via direct asymmetric intramolecular aldolization
Organocatalytic entry to chiral bicyclo[3.n.1]alkanones via direct asymmetric intramolecular aldolization
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DOI：
10.1021/ol051569d
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发表时间：
2005-09-15
期刊：
影响因子：
5.2
通讯作者：
Iwabuchi, Y
中科院分区：
文献类型：
--
作者：
Itagaki, N;Kimura, M;Iwabuchi, Y
描述了内-8-羟基双环[3.3.1]壬南-2-酮和内-7-羟基双环[3.2.1]辛烷-2-酮的简便立体选择性合成，其特点是α-氨基酸催化西格玛对称底物的分子内醛醇缩合。 (4R,2S)-四丁基铵 4-TBDPSoxy-脯氨酸在 3-(4-氧代环己基)丙醛醛醇缩合反应中表现出高对映选择性和高催化效率，得到高度对映体富集的产物 (1S,5R,8R)-8-羟基双环[3.3.1]壬南-2-酮。
The facile stereoselective syntheses of endo-8-hydroxybicyclo[3.3.1]nonan-2-one and endo-7-hydroxybicyclo[3.2.1]octan-2-one, featuring an alpha-amino acid catalyzed intramolecular aldolization of sigma-symmetric substrates, are described. A high enantioselectivity and a high catalytic efficiency have been exhibited by (4R,2S)-tetrabutylammonium 4-TBDPSoxy-prolinate in the aldolization of 3-(4-oxocyclohexyl)propionaidehyde to give highly enantiomerically enriched (1S,5R,8R)-8-hydroxybicyclo[3.3.1]nonan-2-one.