An efficient synthesis of (-)-chloramphenicol via asymmetric catalytic aziridination: A comparison of catalysts prepared from triphenylborate and various linear and vaulted biaryls
An efficient synthesis of (-)-chloramphenicol via asymmetric catalytic aziridination: A comparison of catalysts prepared from triphenylborate and various linear and vaulted biaryls
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DOI：
10.1021/ol010180x
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发表时间：
2001-11-15
期刊：
影响因子：
5.2
通讯作者：
Wulff, WD
中科院分区：
文献类型：
--
作者：
Loncaric, C;Wulff, WD
用三苯硼酸盐和(R)- vapol配体制备手性催化剂，通过不对称催化叠氮化反应，仅用4步就以光学纯形式合成了抗生素(-)-氯霉素。由VAPOL和VANOL配体制备的催化剂比由6,6'-二苯基VAPOL、BINOL和BANOL配体制备的催化剂具有更高的不对称诱导。
[GRAPHICS]The antibiotic (-)-choramphenicol has been synthesized in only four steps from p-nitro-benzaldehyde in optically pure form from an asymmetric catalytic aziridination reaction with a chiral catalyst prepared from triphenylborate and the (R)-VAPOL ligand. Catalysts generated from the VAPOL and VANOL ligands give much higher asymmetric induction than do catalysts prepared from 6,6'-diphenylVAPOL, BINOL, and BANOL ligands.