S(N)2' reaction of organozinc reagents activated by catalytic tBu-P4 base in the presence of LiCl.

S(N)2' reaction of organozinc reagents activated by catalytic tBu-P4 base in the presence of LiCl.
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DOI:
10.1002/chem.200900556
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发表时间:
2009-09
期刊:
影响因子:
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通讯作者:
Koji Kobayashi;M. Ueno;H. Naka;Y. Kondo
Koji Kobayashi;M. Ueno;H. Naka;Y. Kondo
中科院分区:
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文献类型:
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作者:
Koji Kobayashi;M. Ueno;H. Naka;Y. Kondo

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发现tBu-P4碱是用于活化有机锌试剂的优良催化剂。该碱用于在LiCl存在下与各种有机锌试剂反应时促进带有γ-氯化物的α,β-不饱和酯的S(N)2'反应。该反应具有较高的产率和良好的化学选择性和区域选择性。LiCl的作用似乎是α,β-不饱和酯的γ-氯化物的活化,这通过NMR光谱研究证实。
The tBu-P4 base was found to be an excellent catalyst for the activation of organozinc reagents. The base was used to promote the S(N)2' reaction of alpha,beta-unsaturated esters bearing a gamma-chloride in the reactions with various organozinc reagents in the presence of LiCl. The reactions proceeded in high yield with excellent chemo-and regioselectivity. The role of LiCl appears to be the activation of the gamma-chloride of the alpha,beta-unsaturated esters, which was confirmed by NMR spectroscopic study.