Highly diastereoselective synthesis of α-difluoromethyl amines from N-tert-butylsulfinyl ketimines and difluoromethyl phenyl sulfone

Liu J.; Hu J.

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Highly diastereoselective synthesis of α-difluoromethyl amines from N-tert-butylsulfinyl ketimines and difluoromethyl phenyl sulfone

机译：由N-叔丁基亚磺酰基酮亚胺和二氟甲基苯基砜高度非对映选择性合成α-二氟甲基胺

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The first highly efficient and stereoselective difluoromethylation of structurally diverse N-tert-butylsulfinyl ketimines has been achieved with an in situ generated PhSO_2CF_2~- anion, which provides a powerful synthetic method for the preparation of a variety of structurally diverse homochiral α-difluoromethyl tertiary carbinamines, including α-difluoromethyl allylic amines and α-difluoromethyl propargylamines. The stereocontrol mode of the present diastereoselective difluoromethylation of ketimines was found to be different from that of other known fluoroalkylations of N-tert-butylsulfinyl aldimines, which suggests that a cyclic six-mem-bered transition state may be involved in the reaction.

机译：用原位生成的PhSO_2CF_2〜阴离子实现了结构多样的N-叔丁基亚磺酰基酮亚胺的第一个高效立体选择性二氟甲基化反应，这为制备各种结构多样的同手性α-二氟甲基叔卡宾胺提供了有力的合成方法，包括α-二氟甲基烯丙基胺和α-二氟甲基炔丙基胺。发现目前酮亚胺的非对映选择性二氟甲基化的立体控制模式与N-叔丁基亚磺酰基亚胺的其他已知的氟代烷基化的立体控制模式不同，这表明该反应可能涉及环状的六元过渡态。

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《Chemistry: A European journal》 |2010年第37期|共12页
作者
Liu J.; Hu J.;
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正文语种 eng
中图分类应用化学;
关键词
Amines; Difluoromethylation; Fluorine; Ketimines; Nucleophilic addition;

机译：胺;二氟甲基化;氟;酮亚胺;亲核加成;

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专利

1. Highly diastereoselective synthesis of α-difluoromethyl amines from N-tert-butylsulfinyl ketimines and difluoromethyl phenyl sulfone [J] . Liu J., Hu J. Chemistry: A European journal . 2010,第37期

机译：由N-叔丁基亚磺酰基酮亚胺和二氟甲基苯基砜高度非对映选择性合成α-二氟甲基胺
2. Convenient synthesis of difluoromethyl alcohols from both enolizable and non-enolizable carbonyl compounds with difluoromethyl phenyl sulfone [J] . Prakash GKS, Hu JB, Wang Y, European journal of organic chemistry . 2005,第11期

机译：用二氟甲基苯基砜方便地从可烯化和不可烯化的羰基化合物合成二氟甲醇
3. Stereoselective synthesis of γ,δ-unsaturated β-amino sulfones from ellman's N-tert-butylsulfinyl ketimines and methyl Phenyl sulfone [J] . Zhang H., Li Y., Xu F., Synlett . 2012,第17期

机译：由埃尔曼的N-叔丁基亚磺酰基酮亚胺和甲基苯基砜立体选择性合成γ，δ-不饱和β-氨基砜
4. Synthesis of 3-Methyl-1-2-(1-piperidiny) phenyl-butyl Amine [C] . Huixian Liu, Daowei Huang, Yue Zhang International Conference on Chemical, Material and Metallurgical Engineering . 2012

机译：合成3-甲基-1- 2-（1-哌啶）苯基 - 丁胺
5. Part A. Diastereoselective synthesis of protected secondary amines via reduction /alkylation or deprotonation /alkylation of N-diphenylphosphinylimines. Part B. Synthesis of secondary amines via 1,2-addition of organometallic reagents to N-diphenylphosphinylimines and subsequent alkylation [D] . Shin, Hyunshun 2001

机译：A部分：通过N-二苯基膦亚胺的还原/烷基化或去质子化/烷基化的非对映选择性合成保护的仲胺。 B部分：通过将有机金属试剂1,2-加成到N-二苯基膦亚胺和随后的烷基化反应来合成仲胺
6. Conversion of Methyl Ketones and Methyl Sulfones into α-Deutero-αα-Difluoromethyl Ketones and α-Deutero-αα-Difluoromethyl Sulfones in Three Synthetic Steps [O] . Munia F. Sowaileh, Changho Han, Robert A. Hazlitt, -1

机译：通过三个合成步骤将甲基酮和甲基砜转化为α-氘代-αα-二氟甲基酮和α-氘代-αα-二氟甲基砜
7. Nucleophilic Difluoromethylation of Primary Alkyl Halides Using Difluoromethyl Phenyl Sulfone as a Difluoromethyl Anion Equivalent [O] . -1

机译：二氟甲基苯基砜作为二氟甲基阴离子当量的亲烷基卤代核酸二氟甲基化
8. Synthesis of Bromodifluoromethyl Phenyl Sulfide, Sulfoxide and Sulfone [R] . Burton, D. J., Wiemers, D. M. 1981

机译：溴代二氟甲基苯基硫醚，亚砜和砜的合成

Highly diastereoselective synthesis of α-difluoromethyl amines from N-tert-butylsulfinyl ketimines and difluoromethyl phenyl sulfone

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