Unknown

Dataset Information

0

A Regio- and Stereodivergent Synthesis of Homoallylic Amines by a One-Pot Cooperative-Catalysis-Based Allylic Alkylation/Hofmann Rearrangement Strategy.


ABSTRACT: Herein, we report a modular synthetic route to linear and branched homoallylic amines that operates through a sequential one-pot Lewis base/transition-metal catalyzed allylic alkylation/Hofmann rearrangement strategy. This protocol is operationally trivial, proceeds from simple and easily prepared substrates and catalysts, and enables all aspects of regio- and stereoselectivity to be controlled through a conserved experimental protocol. Overall, the high levels of enantio-, regio-, and diastereoselectivity obtained, in concert with the ability to access orthogonally protected or free amines, render this a straightforward and effective approach for the preparation of useful enantioenriched homoallylic amines. We have also demonstrated the utility of the products in the context of pharmaceutical synthesis.

SUBMITTER: Pearson CM 

PROVIDER: S-EPMC7213271 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

altmetric image

Publications

A Regio- and Stereodivergent Synthesis of Homoallylic Amines by a One-Pot Cooperative-Catalysis-Based Allylic Alkylation/Hofmann Rearrangement Strategy.

Pearson Colin M CM   Fyfe James W B JWB   Snaddon Thomas N TN  

Angewandte Chemie (International ed. in English) 20190628 31


Herein, we report a modular synthetic route to linear and branched homoallylic amines that operates through a sequential one-pot Lewis base/transition-metal catalyzed allylic alkylation/Hofmann rearrangement strategy. This protocol is operationally trivial, proceeds from simple and easily prepared substrates and catalysts, and enables all aspects of regio- and stereoselectivity to be controlled through a conserved experimental protocol. Overall, the high levels of enantio-, regio-, and diastereo  ...[more]

Similar Datasets

| S-EPMC2536500 | biostudies-literature
| S-EPMC2528547 | biostudies-literature
| S-EPMC8672708 | biostudies-literature
| S-EPMC4818679 | biostudies-literature
| S-EPMC2993781 | biostudies-literature
| S-EPMC5497580 | biostudies-literature
| S-EPMC4692243 | biostudies-literature
| S-EPMC4902051 | biostudies-other
| S-EPMC2711528 | biostudies-literature
| S-EPMC5213737 | biostudies-literature