New Dihydroxy Bis(Oxazoline)Ligands for the Palladium-Catalyzed Asymmetric Allylic Alkylation:Experimental Investigations of the Origin of the Reversal of the Enantioselectivity

Hassan Ait-Haddou; Olivier Hoarau; Dimitri Cramailere; Frederic Pezet; Jean-Claude Daran; Gilbert G.A.Balavoine

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New Dihydroxy Bis(Oxazoline)Ligands for the Palladium-Catalyzed Asymmetric Allylic Alkylation:Experimental Investigations of the Origin of the Reversal of the Enantioselectivity

机译：钯催化不对称烯丙基烷基化的新型二羟基双（恶唑啉）配体：对映选择性逆转起源的实验研究

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The origin of the reversal of the enantioselectivity in the palladium-catalyzed allylic alkylation of rac-1,3-diphenyl-2-propenyl acetate with dimethyl malonate anion using chiral di-hydroxy bis(oxazoline)"BO"ligands derived from(7S,2S)-(+)-2-amino-l-phenyl-l,3-propanediol was investigated.To determine the structural effects of the dihydroxy BO ligand on this unique phenomenon,new homochiral dihydroxy BO ligands were preparedfrom L-threonine and L-serine and were assessed in the transformation.The results obtained with these novel BO ligands,compared with the one obtained by using the dihydroxy BO ligands derived from(1S,2S)-(+)-2-amino-l-phenyl-1,3-propanediol,reveal that the reversal in the enantioselectivity observed with the dihydroxy BO ligand depends on the structure of the ligand.The effect of different bases used to generate the dimethyl malonate anion was also examined.The results are discussed in terms of the interaction of one hydroxy group in the intermediate pi-allyl palladium complex with the dimethyl malonate anion.

机译：使用手性二羟基双（恶唑啉）“ BO”配体衍生的手性二羟基双（恶唑啉）“ BO”配体，将钯催化的rac-1,3-二苯基-2-丙烯基乙酸酯的钯催化的rac-1,3-二苯基-2-丙烯基乙酸烯丙基烷基化的对映选择性逆转的起源。研究了2S）-（+）-2-氨基-1-苯基-1,3-丙二醇。为确定二羟基BO配体对此独特现象的结构影响，由L-苏氨酸和L制备了新的手性二羟基BO配体这些新型BO配体获得的结果与使用（1S，2S）-（+）-2-氨基-1-苯基-1衍生的二羟基BO配体获得的结果相比，3-丙二醇，揭示了用二羟基BO配体观察到的对映选择性的逆转取决于配体的结构。还研究了用于生成丙二酸二甲酯的不同碱的作用。中间烯丙基palla中一个羟基的相互作用钠与丙二酸二甲酯的阴离子形成络合物。

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《Chemistry: A European journal》 |2004年第3期|共9页
作者
Hassan Ait-Haddou; Olivier Hoarau; Dimitri Cramailere; Frederic Pezet; Jean-Claude Daran; Gilbert G.A.Balavoine;
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正文语种 eng
中图分类化学;
关键词
allylic alkylation; asymmetric catalysis; enantioselectivity; N ligands; palladium;

机译：烯丙基烷基化;不对称催化;对映选择性;N配体;钯;

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1. New Dihydroxy Bis(Oxazoline)Ligands for the Palladium-Catalyzed Asymmetric Allylic Alkylation:Experimental Investigations of the Origin of the Reversal of the Enantioselectivity [J] . Hassan Ait-Haddou, Olivier Hoarau, Dimitri Cramailere, Chemistry: A European journal . 2004,第3期

机译：钯催化不对称烯丙基烷基化的新型二羟基双（恶唑啉）配体：对映选择性逆转起源的实验研究
2. Axially chiral P,S-heterodonor ligands with a binaphthalene framework for palladium-catalyzed asymmetric allylic substitutions: experimental investigation on the reversal of enantioselectivity between different alkyl groups on sulfur atom [J] . Zhang W, Shi M Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2004,第21期

机译：具有双萘骨架的轴向手性P，S-杂配体配体，用于钯催化的不对称烯丙基取代：逆转硫原子上不同烷基之间对映选择性的实验研究
3. Unexpected reversal of the enantioselectivity using chiral quinolylmethyl- and acridininyloxazolines as ligands for asymmetric palladium-catalyzed allylic alkylation [J] . Chelucci G., Saba A., Valenti R., Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2000,第19期

机译：使用手性喹啉基甲基-和cri啶氮基恶唑啉作为不对称钯催化的烯丙基烷基化的配体，意外地逆转了对映选择性
4. D-GLUCOSAMINE DERIVED "UMBRELLA -LIKE" LIGAND IN HIGHLY ENANTIOSELECTIVE PALLADIUM-CATALYZED ALLYLIC ALKYLATIONS(Abstracts) [C] . Tomasz Bauer, Agnieszka Bartoszewicz European Symposium on Organic Chemistry . 2007

机译：D-葡萄糖胺衍生的“伞状”配体在高映选择性钯催化的烯丙基烷基化（摘要）中
5. Ligand design for palladium-catalyzed asymmetric allylic alkylations. Enantioselective synthesis of small bioactive molecules [D] . Zambrano, Jorge Luis 1999

机译：钯催化不对称烯丙基烷基化反应的配体设计。小生物活性分子的对映选择性合成
6. Spiro Indane-Based Phosphine-Oxazolines as Highly Efficient PN Ligands for Enantioselective Pd-Catalyzed Allylic Alkylation of Indoles and Allylic Etherification [O] . Zhongxuan Qiu, Rui Sun, Kun Yang, 2019

机译：基于螺茚满的膦-恶唑啉作为高效PN配体用于对映选择性Pd催化的吲哚烯丙基烷基化和烯丙基醚化
7. Novel ferrocenylphosphine-imines containing a pyridine unit as a new family of chiral ligands:the important influence of the position of the pyridine N-atom on the reactivity and enantioselectivity in palladium-catalyzed asymmetric allylic alkylations [O] . 胡向平, 戴慧聪, 白长敏, 2004

机译：Novel ferrocenylphosphine-imines containing a pyridine unit as a new family of chiral ligands:the important influence of the position of the pyridine N-atom on the reactivity and enantioselectivity in palladium-catalyzed asymmetric allylic alkylations

New Dihydroxy Bis(Oxazoline)Ligands for the Palladium-Catalyzed Asymmetric Allylic Alkylation:Experimental Investigations of the Origin of the Reversal of the Enantioselectivity

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