Asymmetric synthesis of β-amino acids through application of chiral sulfoxide
Asymmetric synthesis of β-amino acids through application of chiral sulfoxide
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DOI：
10.1016/s0957-4166(01)00185-9
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发表时间：
2001-05-08
影响因子：
--
通讯作者：
Bhat, SV
中科院分区：
文献类型：
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作者：
Sivakumar, AV;Babu, GS;Bhat, SV
本文报道了用亚砜类助剂不对称合成β-氨基苯基丙酸的方法.在将（+）-（R）-对甲苯亚磺酰基乙酸叔丁酯的烯醇化锂加成到取代的N-（亚苄基）甲苯-4-磺酰胺中的过程中，实现了高动力学控制的（3R，2S，R-S）-非对映选择性（-60 ℃）。加合物3a与钠汞齐还原裂解产生3-（甲苯-4-磺酰氨基）-3-苯基丙酸叔丁酯5a。将其进行酯水解，随后在液氨中用钠脱甲苯磺酰化，以良好的产率和高91%e. e.得到（S）-β-氨基苯基丙酸。(C)2001爱思唯尔科技有限公司版权所有。
This paper describes asymmetric synthesis of beta -aminophenylpropionic acid through application of a homochiral sulfoxide auxiliary. High kinetically controlled (3R.2S.R-S)-diastereoselectivity (-60 degreesC) is achieved during addition of the lithium enolate of tert-butyl (+)-(R)-p-toluenesulfinylacetate to substituted N-(benzylidene)toluene-4-sulfonamides. The reductive cleavage of adduct 3a with sodium amalgam yielded tert-butyl 3-(toluene-4-sulfonamido)-3-phenylpropionate 5a. which was subjected to ester hydrolysis and subsequent detosylation with sodium in liquid ammonia to yield (S)-beta -aminophenylpropionic acid in good yield and high 91% e.e. (C) 2001 Elsevier Science Ltd. All rights reserved.