Regioselective and stereoselective nucleophilic ring opening reactions of a phenyl-substituted aziridine: enantioselective synthesis of beta-substituted tryptophan, cysteine, and serine derivatives.
Regioselective and stereoselective nucleophilic ring opening reactions of a phenyl-substituted aziridine: enantioselective synthesis of beta-substituted tryptophan, cysteine, and serine derivatives.
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苯基取代的氮丙啶的区域选择性和立体选择性亲核开环反应：β-取代的色氨酸、半胱氨酸和丝氨酸衍生物的对映选择性合成。
DOI：
10.1021/jo010860d
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发表时间：
2002
期刊：
影响因子：
--
通讯作者：
Hruby,VictorJ
中科院分区：
文献类型：
--
作者：
Xiong,Chiyi;Wang,Wei;Cai,Chaozhong;Hruby,VictorJ
建立了β-苯基取代半胱氨酸、色氨酸和丝氨酸衍生物的不对称合成方法。在该方法中，关键中间体3-苯基氮杂环丙烷-2-羧酸酯7由α，β-不饱和酯1通过夏普莱斯不对称双羟基化反应得到。氮杂环丙烷7分别与4-甲氧基苄硫醇、吲哚和醋酸反应，得到β-苯基取代的半胱氨酸、色氨酸和丝氨酸，在C3位有一个干净的SN2型开环。该方法可用于合成多种β取代的新型氨基酸。
The asymmetric synthesis of β-phenyl-substituted cysteine, tryptophan, and serine derivatives was successfully developed. In this approach, the key intermediate, enantiomerically pure 3-phenylaziridine-2-carboxylic ester7, was prepared from α,β-unsaturated ester1by employing the Sharpless asymmetric dihydroxylation. The aziridine7was treated with 4-methoxybenzylthiol, indole, and acetic acid to give β-phenyl-substituted cysteine, tryptophan, and serine, respectively, in a clean SN2 type ring opening at the C3position. This general approach can be used to synthesize a variety of β-substituted novel amino acids.