A catalyst that plays multiple roles:: Asymmetric synthesis of β-substituted aspartic acid derivatives through a four-stage, one-pot procedure
A catalyst that plays multiple roles:: Asymmetric synthesis of β-substituted aspartic acid derivatives through a four-stage, one-pot procedure
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DOI：
10.1021/ol017087t
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发表时间：
2002-02-07
期刊：
影响因子：
5.2
通讯作者：
Lectka, T
中科院分区：
文献类型：
--
作者：
Dudding, T;Hafez, AM;Lectka, T
[图形]报道了一种催化不对称合成P-取代天冬氨酸衍生物的新方法，其中亲核催化剂在一锅法中扮演着四个不同的角色：催化酸性氯化物的脱氢卤化生成酮；催化α-氯胺的脱氢卤化生成相应的亚胺；催化[2+2]-环加成生成中间体β-内酰胺；最后，亲核开环得到光学丰富的β-取代天冬氨酸，具有高的对映选择性和非对映选择性。
[GRAPHICS]e report a new method for the catalytic, asymmetric synthesis of P-substituted aspartic acid derivatives in which the nucleophilic catalyst serves up to four discrete roles in a one-pot procedure: catalytic dehydrohalogenation of acid chlorides to form ketenes; catalytic dehydrohalogenation of alpha-chloroamines to form the corresponding imines; catalyzed [2 + 2]-cycloaddition to produce intermediate acyl beta-lactams; and finally, nucleophilic ring opening to afford optically enriched beta-substituted aspartic acids in high en antioselectivity and diastereoselectivity.