Chiral lithium amido sulfide ligands for asymmetric addition reactions of alkyllithium reagents to aldehydes
Chiral lithium amido sulfide ligands for asymmetric addition reactions of alkyllithium reagents to aldehydes
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DOI：
10.1016/s0957-4166(02)00864-9
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发表时间：
2003-02-21
影响因子：
--
通讯作者：
Hilmersson, G
中科院分区：
文献类型：
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作者：
Granander, J;Sott, R;Hilmersson, G
以苯丙氨酸为原料合成了六个手性氨基硫醚。苯甘氨酸和缬氨酸。这些氨基硫醚被用作手性配体，在低温下正丁基锂和甲基锂对各种醛的不对称加成反应中。最高的立体选择性，得到与berizaldehyde。得到对映体过量分别> 98.5%和95%的1-苯基-1-戊醇和1-苯基-1-乙醇。这些立体选择性显着，高于醚类似物诱导的。(C)2003爱思唯尔科技有限公司版权所有。
Six chiral amino sulfides have been synthesised from the amino acids phenylalanine. phenylglycine and valine. These amino sulfides were used as chiral ligands in the asymmetric addition of n-butyllithium and metyllithium to various aldehydes at low temperatures. The highest stereoselectivities were obtained with berizaldehyde. resulting in 1-phenyl-1-pentanol and 1-phenyl-1-ethanol in enantiomeric excesses of > 98.5 and 95% respectively. These stereoselectivities were significantly, higher than those induced by the ether analogues. (C) 2003 Elsevier Science Ltd. All rights reserved.