THE USE OF CYSTEINE-DERIVED AND SERINE-DERIVED THIAZOLIDINETHIONES AND OXAZOLIDINETHIONES AS EFFICIENT CHIRAL AUXILIARIES IN ALDOL CONDENSATIONS
THE USE OF CYSTEINE-DERIVED AND SERINE-DERIVED THIAZOLIDINETHIONES AND OXAZOLIDINETHIONES AS EFFICIENT CHIRAL AUXILIARIES IN ALDOL CONDENSATIONS
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DOI：
10.1021/jo00387a016
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发表时间：
1987-05-29
影响因子：
3.6
通讯作者：
MILLER, MJ
中科院分区：
文献类型：
--
作者：
HSIAO, CN;LIU, L;MILLER, MJ
半胱氨酸衍生的噻唑烷硫酮和丝氨酸衍生的恶唑烷硫酮在硼和锡介导的醇醛缩合中充当有效的手性助剂。与各种简单醛的缩合以高化学和光学收率产生了预期的赤式产物。这些手性助剂的其他优点是易于通过甲醇解或羟氨解去除以及它们的实际可回收性。
Cysteine-derived thiazolidinethiones and serine-derived oxazolidinethiones serve as efficient chiral auxiliaries in boron- and tin-mediated aldol condensations. The condensations with a variety of simple aldehydes produced the expected erythro products in high chemical and optical yields. Additional advantages of these chiral auxiliaries were the ease of removal by methanolysis or hydroxaminolysis and their practical recyclability.