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Chiral Phosphoroamide Organocatalyzed Asymmetric Michael Addition of Nitrostyrenes

Author: WuRongHua
Tutor: WangYouMing
School: Nankai University
Course: Organic Chemistry
Keywords: Chiral phosphorus amide Michael addition reaction Enantioselectivity 2 - hydroxy - 1 ,4 - naphthoquinone Nitroolefins Bond donor catalyst
CLC: O643.32
Type: Master's thesis
Year: 2011
Downloads: 48
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Abstract


In this thesis, a similar structure with thiourea chiral (thio) phosphoramidite catalyzed 2 - hydroxy-1 ,4 - naphthoquinone asymmetric Michael addition reaction of β-nitro- ene , the development of a new type of efficient chiral bond donor dual function catalyst. Due to the structural diversity of phosphorus compounds , can easily by varying the substituents on the phosphorus atom to regulate the catalytic activity , the development of a novel organic catalysts for different reactions , which broke through the double hydrogen bond donor thiourea derivatives led the body of organic bound catalyst and rich double bond donor catalyst type . (1R, 2R)-N, N- dimethyl-1 ,2 - cyclohexane diamine and (R)-Betti alkali , and (S)-Betti alkali as raw materials, design and synthesis of a series of chiral (thio ) phosphoryloxymethyl diamine catalyst, also prepared by a single bond donor phosphoroamidothioate catalyst is used for comparison . 2 - hydroxy - 1 ,4 - naphthoquinone (E)-β- nitrostyrene Michael plus a model reaction investigated the catalytic activity of the different structures of the chiral phosphorus (thio) amide and enantioselectivity found that all of the catalyst can be an effective catalytic reaction , in a relatively short period of time with a higher yield and ee worth to the target addition product . Wherein the double hydrogen bond donor the Body (thio) showed phosphoryloxymethyl diamine for the Body Thioxophosphamide better catalytic activity than the single hydrogen . In addition , the the diamine phosphorohydrazonothionate structure of the reaction is also very obvious , under the optimal reaction conditions , derived from 1,2 - cyclohexanediamine C2 symmetry of phenyl phosphorohydrazonothionate diamine catalyst shows efficient catalytic activity, but also exhibit a good asymmetric induction ability , either aliphatic or aromatic nitro alkenyl obtain a near perfect mapping selection result (ee value GT ; 99 % ) . In addition , the catalytic system is equally applicable to the less reactive α-methyl- nitro - ene , obtained by reaction of a good non - mapping and enantioselectivity in the reaction process is formed only ee value of 91% of the single non- enantiomer .

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CLC: > Mathematical sciences and chemical > Chemistry > Physical Chemistry ( theoretical chemistry ),chemical physics > Chemical kinetics,catalysis > Catalytic > Catalytic reaction
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