Diastereoselective Allylation and Crotylation Reactions of Aldehydes with Potassium Allyl- and Crotyltrifluoroborates under Lewis Acid Catalysis

Diastereoselective Allylation and Crotylation Reactions of Aldehydes with Potassium Allyl- and Crotyltrifluoroborates under Lewis Acid Catalysis
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Lewis酸催化下醛与烯丙基三氟硼酸钾和巴豆基三氟硼酸钾的非对映选择性烯丙基化和巴豆酰化反应

DOI:
10.1055/s-2000-6303
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发表时间:
2000
期刊:
Synthesis
影响因子:
--
通讯作者:
A. Lough
A. Lough
中科院分区:
--
文献类型:
--
作者:
R. Batey;A. N. Thadani;D. Smil;A. Lough

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烯丙基和巴豆基三氟硼酸钾在各种刘易斯酸催化下与醛反应,生成相应的高烯丙醇。在所考察的刘易斯酸中,以化学计量或催化方式使用的BF 3 dad OEt 2能最有效地催化该反应.空气和湿气稳定的有机三氟硼酸钾盐与各种烷基、α-或B -取代的烷基和芳基醛反应,并以高产率和高非对映选择性产生加合物。
: Potassium allyl-and crotyltrifluoroborates react with aldehydes in a process catalyzed by a variety of Lewis acids, to give the corresponding homoallylic alcohols. Of the Lewis acids examined, BF 3 ◊ OEt 2 , used either stoichiometrically or catalytically, was found to most efficiently catalyze this reaction. The air and moisture stable potassium organotrifluoroborate salts react with a variety of alkyl, a - or b - substituted alkyl, and aryl aldehydes, and lead to the adducts in high yield and with high diastereoselectivity.