A new class of nitrogen based chiral ligands:: 2H-1,3-benzoxazines.: Ligand synthesis, X-ray structural studies and asymmetric catalysis
A new class of nitrogen based chiral ligands:: 2H-1,3-benzoxazines.: Ligand synthesis, X-ray structural studies and asymmetric catalysis
复制标题
DOI：
10.1016/j.jorganchem.2004.11.047
复制
发表时间：
2005-04-15
影响因子：
2.3
通讯作者：
Perlmutter, P
中科院分区：
文献类型：
--
作者：
Thienthong, N;Perlmutter, P
以水杨胺和(-)-薄荷酮为原料，以苯并恶嗪为核心，分三步合成了一类新的手性配体，如(-)-9。应用(-)-9钯催化丙二酸二甲酯取代1,3-二苯基-2-丙烯乙酸酯，对映体选择性高达62%ee。在不对称硅化氢反应和二乙基锌反应中，Ees分别为42%和20%。(c) 2004 Elsevier B.V.版权所有
A new class of chiral ligands, e.g., (-)-9, based on the benzoxazine nucleus, has been designed and synthesized in three steps from the commercially available starting materials salicylamide and (-)-menthone. Application of (-)-9 in the palladium catalyzed-allylic substitution of 1,3-diphenyl-2-propenylacetate with dimethyl malonate gave enantio selectivities of up to 62%ee. Ees of 42% and 20% in asymmetric hydrosilylations and diethylzinc additions, respectively, were also obtained. (c) 2004 Elsevier B.V. All rights reserved.