Catalytic asymmetric synthesis of enantioenriched beta-nitronitrile bearing a C-CF3 stereogenic center

Jakhar Ajay; Kumari Prathibha; Nazish Mohd; Khan Noor-ul H.; Kureshy Rukhsana I.; Abdi Sayed H. R.; Suresh E.

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Catalytic asymmetric synthesis of enantioenriched beta-nitronitrile bearing a C-CF3 stereogenic center

机译：携带C-CF3立体中心的催化不对称合成糖醛β-氮腈

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CF3 substituted beta-nitronitriles with an all-carbon quaternary stereogenic center have been synthesized via asymmetric cyanation reaction. In situ generated chiral Ti-IV salen complexes were used as catalysts for asymmetric addition of TMSCN to nitroolefins containing a trifluoromethylated prochiral center in the beta-position, to afford the corresponding beta-nitronitriles in excellent yield (up to 93%) with good enantioselectivity (up to 99%). This newly developed catalytic protocol led to the efficient synthesis of useful but challenging chiral alpha,alpha'-disubstituted beta-amino acids.

机译：通过不对称的氰化反应合成CF3具有全碳季型立体转立型中心的β-氮腈。原位生成的手性Ti-IV Salen络合物用作催化剂，用于在β-位置中含有三氟甲基化的盆景中心的亚甲磺酸酯的不对称加法，得到相应的β-氮腈，其优异的产率（高达93％）具有良好的对映选择性（高达99％）。这种新开发的催化方案导致了有效但挑战性的手性α，α'-二取代的β-氨基酸的有效合成。

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《RSC Advances》 |2016年第36期|共6页
作者
Jakhar Ajay; Kumari Prathibha; Nazish Mohd; Khan Noor-ul H.; Kureshy Rukhsana I.; Abdi Sayed H. R.; Suresh E.;
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作者单位

CSIR Cent Salt &

Marine Chem Res Inst Inorgan Mat &

Catalysis Div GB Marg Bhavnagar 364002 Gujarat India;

CSIR Cent Salt &

Marine Chem Res Inst Inorgan Mat &

Catalysis Div GB Marg Bhavnagar 364002 Gujarat India;

CSIR Cent Salt &

Marine Chem Res Inst Inorgan Mat &

Catalysis Div GB Marg Bhavnagar 364002 Gujarat India;

CSIR Cent Salt &

Marine Chem Res Inst Inorgan Mat &

Catalysis Div GB Marg Bhavnagar 364002 Gujarat India;

CSIR Cent Salt &

Marine Chem Res Inst Inorgan Mat &

Catalysis Div GB Marg Bhavnagar 364002 Gujarat India;

CSIR Cent Salt &

Marine Chem Res Inst Inorgan Mat &

Catalysis Div GB Marg Bhavnagar 364002 Gujarat India;

CSIR Cent Salt &

Marine Chem Res Inst Acad Sci &

Innovat Res GB Marg Bhavnagar 364002 Gujarat India;

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中图分类化学;
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1. Catalytic asymmetric synthesis of enantioenriched beta-nitronitrile bearing a C-CF3 stereogenic center [J] . Jakhar Ajay, Kumari Prathibha, Nazish Mohd, RSC Advances . 2016,第36期

机译：携带C-CF3立体中心的催化不对称合成糖醛β-氮腈
2. Catalytic Asymmetric Synthesis of Enantioenriched Heterocycles Bearing a CCF3 Stereogenic Center [J] . Huang Yi-Yong, Yang Xing, Chen Zhuo, Chemistry: A European journal . 2015,第24期

机译：具有CCF3立体中心的对映体富集杂环的催化不对称合成
3. Catalytic Asymmetric Synthesis of Enantioenriched Heterocycles Bearing a CCF3 Stereogenic Center [J] . Huang Yi-Yong, Yang Xing, Chen Zhuo, Chemistry: A European journal . 2015,第24期

机译：具有CCF3立体中心的对映体富集杂环的催化不对称合成
4. Synthesis of Rhodium Allyl Complexes Having a Stereogenic Center on the Metal Center [C] . Yasutaka Kataoka, Takahiro Akashi, Tsuneaki Yamagata, Symposium on Organometallic Chemistry . 2004

机译：在金属中心含有立体元中心的铑烯丙基配合物的合成
5. I. Studies on the organocatalytic formation of quaternary stereocenters. ii. Studies on the claisen rearrangement as a route to quaternary stereocenters. iii. Asymmetric synthesis of aldehydes bearing quaternary carbon centers via the decarboxylative asymmetric allylic alkylation. [D] . Alberch, Eduardo. 2013

机译：I.季铵立体中心的有机催化形成研究。 ii。关于克莱森重排作为四元立体中心路径的研究。 iii。通过脱羧不对称烯丙基烷基化反应不对称合成带有季碳中心的醛。
6. Enantioselective Synthesis of All-Carbon Quaternary Stereogenic Centers by Catalytic Asymmetric Conjugate Additions of Alkyl and Aryl Aluminum Reagents to Five- Six- and Seven-Membered-Ring β-Substituted Cyclic Enones [O] . Tricia L. May, M. Kevin Brown, Amir H. Hoveyda -1

机译：烷基和芳烃铝试剂催化不对称共轭加成五元六元和七元环β-取代的环烯酮的全碳四元立体中心的对映选择性合成
7. The Fluoro-PausonKhand Reaction in the Synthesis of Enantioenriched Nitrogenated Bicycles Bearing a Quaternary CF Stereogenic Center [O] . -1

机译：含有季型CF立体中心亚氨基硫化氮自行车的合成中的氟-POUSONK手反应

Catalytic asymmetric synthesis of enantioenriched beta-nitronitrile bearing a C-CF3 stereogenic center

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