有机催化对映选择性合成α-羟基膦酸盐的两种非对映异构体。
Organocatalytic enantioselective synthesis of both diastereomers of alpha-hydroxyphosphinates.
机构信息
Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA.
出版信息
J Org Chem. 2010 Feb 19;75(4):1101-6. doi: 10.1021/jo9022099.
Abstract
Racemic alpha-acylphosphinates and formylphosphinate hydrate were used directly as the substrates in a proline derivative-catalyzed cross aldol reaction with ketones. Because of the preexisting phosphorus stereogenic center, a mixture of two diastereomers of the corresponding alpha-hydroxyphosphinates was obtained in this reaction. Good to high enantioselectivities (up to 99% ee) were obtained simultaneously for the two diastereomers in good yields. Good diastereoselectivities were also obtained when the reaction generates an additional carbon stereogenic center.
摘要
外消旋的α-酰基膦酸盐和甲酰基膦酸盐水合物被直接用作脯氨酸衍生物催化的与酮的交叉羟醛反应的底物。由于预先存在的磷手性中心，在该反应中得到了相应的α-羟基膦酸盐的两种非对映异构体的混合物。两种非对映异构体的产率都很高，同时获得了良好到高的对映选择性（高达 99%ee）。当反应生成额外的碳手性中心时，也获得了良好的非对映选择性。
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