由（S）-N-丙烯酰基-5,5-二甲基恶唑烷-2-酮超季铵盐衍生物不对称合成2-烷基和2-芳基-3-氨基丙酸（β2-氨基酸）
Asymmetric synthesis of 2-alkyl- and 2-aryl-3-aminopropionic acids (beta2-amino acids) from (S)-N-acryloyl-5,5-dimethyloxazolidin-2-one SuperQuat derivatives.
作者信息
Beddow James E, Davies Stephen G, Smith Andrew D, Russell Angela J
机构信息
Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK.
出版信息
Chem Commun (Camb). 2004 Dec 7(23):2778-9. doi: 10.1039/b410938d. Epub 2004 Oct 22.
DOI:10.1039/b410938d
PMID:15568113
Abstract
Conjugate addition of lithium amides to (S)-N-acryloyl- or (S)-N-2'-alkylacryloyloxazolidinones and alkylation or protonation of the resulting enolates with 2-pyridone respectively provides a highly stereoselective and product complementary route to a range of (R)- and (S)-2-alkyl-3-aminopropionic acids in good yield and in high ee.
摘要
将锂酰胺与(S)-N-丙烯酰基-或(S)-N-2'-烷基丙烯酰基恶唑烷酮进行共轭加成，然后分别用2-吡啶酮对所得烯醇盐进行烷基化或质子化，可提供一条高立体选择性且产物互补的路线，以良好的产率和高对映体过量得到一系列(R)-和(S)-2-烷基-3-氨基丙酸。
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