FORMATION, STRUCTURES, AND REACTIONS OF SELECTED ALPHA'-LITHIOALLYL AMIDES
FORMATION, STRUCTURES, AND REACTIONS OF SELECTED ALPHA'-LITHIOALLYL AMIDES
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DOI：
10.1021/jo00263a037
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发表时间：
1989-01-20
影响因子：
3.6
通讯作者：
LEE, B
中科院分区：
文献类型：
--
作者：
BEAK, P;LEE, B
Lithiations of theselected allyl amides 6, 10, 14, and 17 give the'-lithioallyl amides 7, 11, 15, and 18. The structures of 7, 11, and 18 are characterized by theirNMR spectra. Electrophilic substitutions of these reagents are usually regioselectiveat the^'-position, but there are exceptions. In situ lithiation-electrophilic substitutions are effective for 10 and 17 with LiTMP-(CH3) 3SiCl, n-BuLi-C6H5CH2Cl, and n-BuLi-Cl (CH2) 4Cl. Hydrogendeuterium isotope effects are consistent with diastereoselective removal of a pseudoequatorial proton from 17. The lithiations are suggested to occur in an amide-organolithium complex and mostreadily in systems that can achieve a Z conformation.
