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Literature DB >> 22706891

Catalytic enantioselective tert-aminocyclization by asymmetric binary acid catalysis (ABC): stereospecific 1,5-hydrogen transfer.

Liujuan Chen¹, Long Zhang, Jian Lv, Jin-Pei Cheng, Sanzhong Luo.

Abstract

Selective H transfer by ABC: A new asymmetric binary acid catalyst was developed to promote 1,5-H transfer specifically and stereoselectively in tert-aminocyclization reactions with excellent activity, high enantioselectivity, and broad substrate scope. The H atom (in red) was proven to transfer through a stereospecific suprafacial pathway (see scheme).

Entities: Chemical

Year: 2012 PMID： 22706891 DOI： 10.1002/chem.201201532

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

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Cited

18 in total

1. Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with ortho-Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine.

Authors: Matthew T Richers; Indubhusan Deb; Alena Yu Platonova; Chen Zhang; Daniel Seidel
Journal: Synthesis (Stuttg) Date: 2013-10-06 Impact factor: 3.157

2. Redox-neutral α-C-H bond functionalization of secondary amines with concurrent C-P bond formation/N-alkylation.

Authors: Deepankar Das; Daniel Seidel
Journal: Org Lett Date: 2013-08-19 Impact factor: 6.005

3. C-H functionalization of cyclic amines: redox-annulations with α,β-unsaturated carbonyl compounds.

Authors: YoungKu Kang; Matthew T Richers; Conrad H Sawicki; Daniel Seidel
Journal: Chem Commun (Camb) Date: 2015-07-07 Impact factor: 6.222

4. Redox-Neutral Aromatization of Cyclic Amines: Mechanistic Insights and Harnessing of Reactive Intermediates for Amine α- and β-C-H Functionalization.

Authors: Longle Ma; Anirudra Paul; Martin Breugst; Daniel Seidel
Journal: Chemistry Date: 2016-11-09 Impact factor: 5.236

10. Metal-free α-amination of secondary amines: computational and experimental evidence for azaquinone methide and azomethine ylide intermediates.

Authors: Arne Dieckmann; Matthew T Richers; Alena Yu Platonova; Chen Zhang; Daniel Seidel; K N Houk
Journal: J Org Chem Date: 2013-04-02 Impact factor: 4.354

Catalytic enantioselective tert-aminocyclization by asymmetric binary acid catalysis (ABC): stereospecific 1,5-hydrogen transfer.

1. Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with ortho-Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine.

2. Redox-neutral α-C-H bond functionalization of secondary amines with concurrent C-P bond formation/N-alkylation.

3. C-H functionalization of cyclic amines: redox-annulations with α,β-unsaturated carbonyl compounds.

4. Redox-Neutral Aromatization of Cyclic Amines: Mechanistic Insights and Harnessing of Reactive Intermediates for Amine α- and β-C-H Functionalization.

5. Redox-neutral α-arylation of amines.

6. Redox-neutral copper(II) carboxylate catalyzed α-alkynylation of amines.

7. Intramolecular Redox-Mannich Reactions: Facile Access to the Tetrahydroprotoberberine Core.

8. Cascade cyclizations of acyclic and macrocyclic alkynones: studies toward the synthesis of phomactin A.

9. Redox-neutral α,β-difunctionalization of cyclic amines.

10. Metal-free α-amination of secondary amines: computational and experimental evidence for azaquinone methide and azomethine ylide intermediates.