Synthesis of α-methyl kainic acid by stereospecific lithiation-dearomatizing cyclization of a chiral benzamide
Synthesis of α-methyl kainic acid by stereospecific lithiation-dearomatizing cyclization of a chiral benzamide
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DOI：
10.1016/s0040-4039(03)00570-7
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发表时间：
2003-04-14
影响因子：
1.8
通讯作者：
Menet, CJ
中科院分区：
文献类型：
--
作者：
Clayden, J;Knowles, FE;Menet, CJ
N-α-甲基苄基苯甲酰胺的立体定向锂化合成了构型稳定的叔苄基硫化物，它们经历了立体定向脱芳烃环化反应，立体化学保留率为99%。这些产物是部分饱和的异吲哚类化合物，带有一个新的完全取代的立体生成中心。一个十步的序列将其中一个产物转化为红藻氨酸的α-甲基类似物。(C)2003爱思唯尔科学有限公司。保留所有权利。
Stereospecific lithiation of N-alpha-methylbenzyl benzamides gives configurationally stable tertiary benzyllithiums which undergo a stereospecific dearomatizing cyclization with >99% retention of stereochemistry. The products are partially saturated isoindolinones which carry a new fully-substituted stereogenic centre. A ten-step sequence converts one of these products to the alpha-methyl analogue of kainic acid. (C) 2003 Elsevier Science Ltd. All rights reserved.