REACTION OF 2-ARYL-3-(N,N-DIMETHYLAMINO)-1-PROPENES AND THEIR CORRESPONDING QUATERNARY AMMONIUM-SALTS WITH ORGANOMETALLIC SPECIES AND REDUCING AGENTS
REACTION OF 2-ARYL-3-(N,N-DIMETHYLAMINO)-1-PROPENES AND THEIR CORRESPONDING QUATERNARY AMMONIUM-SALTS WITH ORGANOMETALLIC SPECIES AND REDUCING AGENTS
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DOI：
10.1021/jo00392a035
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发表时间：
1987-08-07
影响因子：
3.6
通讯作者：
LAYMAN, WJ
中科院分区：
文献类型：
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作者：
GUPTON, JT;LAYMAN, WJ
鉴于Richey2最近对1-芳基-3-(JV，JV-二甲氨基)-L丙烯与有机锂试剂反应的研究，我们认为这项工作是有趣和有用的。例如，里奇曾报道，在回流正己烷中，正丁基锂与1-苯基-3-(N/V-二甲氨基)-1-丙烯反应生成的主要反应产物是L-(/V，/V-二甲氨基)-2-苄基己烷。有人认为，烯丙基胺通过与锂配位，促进了有机金属试剂与双键的加成。Goering3和他的同事最近也报道了类似的烯丙基碳酸酯与格氏试剂在不同铜(I)盐影响下的交叉偶联反应。一个特别令我们感兴趣的例子是在3-氢-2-苯基-2-丙醇的异戊酸酯中区域选择性地加成正丁基溴化镁，以得到3-氢-2-丙醇。
We believe this work to be interesting and useful in light of the recent studies by Richey2 on the reaction of 1-aryl-3-(JV, JV-dimethylamino)-l-propenes with organo-lithium reagents. For example, Richey has reported that l-(/V,/V-dimethylamino)-2-benzylhexane is produced as the major reaction product by the treatment of n-butyllithium with 1-phenyl-3-(N./V-dimethylamino)-1-propene in re-fluxing hexane. It has been suggested that the allylic amine group facilitates the addition of the organometallic reagent to the double bond by coordination with lithium. Goering3 and co-workers have also recently reported on the cross-coupling reactions of analogous allylic carbox-ylates with Grignard reagents under the influence of various Cu (I) salts. One example that was particularly intriguing to us was the regioselective addition of n-bu-tylmagnesium bromide to the pivalate ester of 3-deuterio-2-phenyl-2-propenol to give 3-deuterio-2-