Organocatalytic Enantioselective Higher‐Order Cycloadditions of In Situ Generated Amino Isobenzofulvenes | Zendy

Donslund Bjarke S. | Zendy; Monleón Alicia | Zendy; Palazzo Teresa A. | Zendy; Christensen Mette Louise | Zendy; Dahlgaard Anne | Zendy; Erickson Jeremy D. | Zendy; Jørgensen Karl Anker | Zendy

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Organocatalytic Enantioselective Higher‐Order Cycloadditions of In Situ Generated Amino Isobenzofulvenes

Author(s) -

Donslund Bjarke S.,

Monleón Alicia,

Palazzo Teresa A.,

Christensen Mette Louise,

Dahlgaard Anne,

Erickson Jeremy D.,

Jørgensen Karl Anker

Publication year - 2018

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201710694

Subject(s) - enantioselective synthesis , cycloaddition , chemistry , indene , catalysis , in situ , organocatalysis , stereochemistry , in silico , combinatorial chemistry , medicinal chemistry , organic chemistry , biochemistry , gene

The [8+2] cycloaddition of indene‐2‐carbaldehydes and nitro olefins is described to provide benzonorbornene scaffolds in a highly peri‐, diastereo‐, and enantioselective fashion in the presence of a C 2 ‐symmetric aminocatalyst. This reaction, which proceeds through a transient semi‐aromatic amino isobenzofulvene, represents the first example of catalytic formation and transformation of these species. Quantum chemical calculations suggest a kinetically controlled stepwise mechanism where the stereochemistry is determined in the first bond‐forming event. Beyond the useful [8+2] cycloadducts, [10+4] cycloadducts have been identified in silico as potential off‐pathway intermediates.

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