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Literature DB >> 21434633

Chiral Brønsted acid catalysis for enantioselective Hosomi-Sakurai reaction of imines with allyltrimethylsilane.

Norie Momiyama¹, Hayato Nishimoto, Masahiro Terada.

Abstract

The chiral Brønsted acid (1b or 1c) has been shown to initiate the Hosomi-Sakurai reaction of imines with excellent enantioselectivities. The combined Brønsted acid system has been developed to offer a new class of chiral Brønsted acid catalysis. The present system proceeds through regeneration of the chiral Brønsted acid by proton transfer from additional Brønsted acid to silylated chiral Brønsted acid, a newly elucidated mechanism for the role of the additional Brønsted acid.

Entities: Chemical

Year: 2011 PMID： 21434633 DOI： 10.1021/ol200595b

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

5 in total

1. N-Heterocyclic Carbene and Chiral Brønsted Acid Cooperative Catalysis for a Highly Enantioselective [4+2] Annulation.

Authors: Dian-Feng Chen; Tomislav Rovis
Journal: Synthesis (Stuttg) Date: 2016-11-18 Impact factor: 3.157

2. Lewis Acid Catalyzed Borotropic Shifts in the Design of Diastereo- and Enantioselective γ-Additions of Allylboron Moieties to Aldimines.

Authors: Farid W van der Mei; Hiroshi Miyamoto; Daniel L Silverio; Amir H Hoveyda
Journal: Angew Chem Int Ed Engl Date: 2016-03-09 Impact factor: 15.336

Chiral Brønsted acid catalysis for enantioselective Hosomi-Sakurai reaction of imines with allyltrimethylsilane.

1. N-Heterocyclic Carbene and Chiral Brønsted Acid Cooperative Catalysis for a Highly Enantioselective [4+2] Annulation.

2. Lewis Acid Catalyzed Borotropic Shifts in the Design of Diastereo- and Enantioselective γ-Additions of Allylboron Moieties to Aldimines.

3. Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols.

4. Early Main Group Metal Catalysts for Imine Hydrosilylation.

5. Insights into LiAlH₄ Catalyzed Imine Hydrogenation.

Chiral Brønsted acid catalysis for enantioselective Hosomi-Sakurai reaction of imines with allyltrimethylsilane.

1. N-Heterocyclic Carbene and Chiral Brønsted Acid Cooperative Catalysis for a Highly Enantioselective [4+2] Annulation.

2. Lewis Acid Catalyzed Borotropic Shifts in the Design of Diastereo- and Enantioselective γ-Additions of Allylboron Moieties to Aldimines.

3. Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols.

4. Early Main Group Metal Catalysts for Imine Hydrosilylation.

5. Insights into LiAlH4 Catalyzed Imine Hydrogenation.

5. Insights into LiAlH₄ Catalyzed Imine Hydrogenation.