Addition of kinetic boron enolates generated from β-alkoxy methyl ketones to aldehydes. Density functional theory calculations on the transition structures
Addition of kinetic boron enolates generated from β-alkoxy methyl ketones to aldehydes. Density functional theory calculations on the transition structures
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DOI：
10.1016/j.tet.2009.08.042
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发表时间：
2009-10-17
期刊：
影响因子：
2.1
通讯作者：
Tiekink, Edward R. T.
中科院分区：
文献类型：
--
作者：
Dias, Luiz C.;Pinheiro, Savio M.;Tiekink, Edward R. T.
本文报道了1,2-syn -烷氧基甲基酮与非手性醛的硼烯醇醛反应中，当-烷氧基保护基团是苄基缩醛的一部分时，得到了良好到极好的1,5抗立体诱导反应。我们还利用密度泛函理论（B3LYP）和Moller-Plesset微扰理论（MP2）计算，研究了配体对硼的影响，α -、β -和γ -取代基以及β -烷氧基保护基对硼烯醇酯的影响。2009爱思唯尔有限公司版权所有，
Herein we report that good to excellent levels of 1,5-anti stereoinduction are obtained in boron enolate aldol reactions of 1,2-syn beta-alkoxy methyl ketones with achiral aldehydes, when the beta-alkoxy protecting group is part of a benzylidene acetal. We have also investigated the effects of the ligands on boron, the alpha-, beta-, and gamma-substituents and the beta-alkoxy protecting group on the boron enolates, using density functional theory (B3LYP) and Moller-Plesset perturbation theory (MP2) calculations. (C) 2009 Elsevier Ltd. All rights reserved,