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An analysis of the complementary stereoselective alkylations of imidazolidinone derivatives toward α-quaternary proline-based amino amides

机译:咪唑啉酮衍生物向α-季脯氨酸基氨基酰胺的互补立体选择性烷基化的分析

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摘要

Alkylations of proline-based imidazolidinones are described based on the principle of self-regeneration of stereocenters (SRS), affording high levels of either the cis or trans configured products. Stereoselectivity is dictated solely on the nature of the “temporary” group, where isobutyraldehyde-derived imidazolidinones provide the cis configured products and 1-naphthaldehyde-derived imidazolidinones afford the complementary trans configured products. These stereodivergent products can be readily cleaved to afford both α-alkylated proline enantiomers from readily available L-proline. A series of imidazolidinones were alkylated to investigate the origin of the anti-selectivity. Potential contributions toward the observed anti-selectivity are discussed on the basis of these experiments, suggesting a refined hypothesis for selectivity may be in order.
机译:基于脯氨酸中心(SRS)的自我再生原理,描述了脯氨酸基咪唑烷酮的烷基化,可提供高水平的顺式或反式构型产物。立体选择性仅取决于“临时”基团的性质,其中异丁醛衍生的咪唑烷酮提供顺式构型的产物,而1-萘醛衍生的咪唑烷酮提供互补的反式构型的产物。这些立体发散产物可以容易地裂解以从容易获得的L-脯氨酸得到两种α-烷基化的脯氨酸对映体。一系列咪唑烷酮被烷基化以研究抗选择性的起源。在这些实验的基础上讨论了对观察到的抗选择性的潜在贡献,表明对选择性的精确假设可能是有序的。

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