Asymmetric synthesis of β2-amino acids:: 2-substituted-3-aminopropanoic acids from N-acryloyl SuperQuat derivatives
Asymmetric synthesis of β2-amino acids:: 2-substituted-3-aminopropanoic acids from N-acryloyl SuperQuat derivatives
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DOI：
10.1039/b707689d
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发表时间：
2007-01-01
影响因子：
3.2
通讯作者：
Thomson, James E.
中科院分区：
文献类型：
--
作者：
Beddow, James E.;Davies, Stephen G.;Thomson, James E.
二苄基氨基锂与（S）-N（3）-丙烯酰基-4-异丙基-5，5-二甲基恶唑烷-2-酮的共轭加成（衍生自L-缬氨酸）和所得β-氨基烯醇化锂的烷基化，在脱保护后，以良好的产率和高ee提供了一系列（S）-2-烷基-3-氨基丙酸。一系列仲氨基化锂与（S）-N（3）-N（3）-（2 '-烷基丙烯酰基）-4-异丙基-5，5-二甲基恶唑烷-2-酮，用2-吡啶酮非对映选择性质子化，和随后的脱保护以良好的产率和高ee得到一系列（R）-2-烷基-和（R）-2-芳基-3-氨基丙酸。另外，硼介导的β-氨基N-酰基恶唑烷酮的羟醛缩合反应是合成一系列β-氨基-β ′-羟基N-酰基恶唑烷酮的高度非对映选择性方法。
Conjugate addition of lithium dibenzylamide to (S)-N(3)-acryloyl-4-isopropyl-5,5-dimethyloxazolidin-2-one ( derived from L-valine) and alkylation of the resultant lithium beta-amino enolate provides, after deprotection, a range of (S)-2-alkyl-3-aminopropanoic acids in good yield and high ee. Alternatively, via a complementary pathway, conjugate addition of a range of secondary lithium amides to (S)-N(3)-(2'-alkylacryloyl)-4-isopropyl-5,5-dimethyloxazolidin-2-ones, diastereoselective protonation with 2-pyridone, and subsequent deprotection furnishes a range of (R)-2-alkyl- and (R)-2-aryl-3-aminopropanoic acids in good yield and high ee. Additionally, the boron-mediated aldol reaction of beta-amino N-acyl oxazolidinones is a highly diastereoselective method for the synthesis of a range of beta-amino-beta'-hydroxy N-acyl oxazolidinones.