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Cation-directed atropselective synthesis of BINOL derivatives

Abstract:

The use of chiral counterions to facilitate enantioselective mono-C-alkylation of enolates has been explored extensively over the past century. We have demonstrated that an alternative mode of reactivity – O-alkylation – predominates if the C-alkylation is impeded. We have applied this concept to the atropselective dynamic kinetic resolution of 1-aryl-2-tetralones, leading to an organocatalytic synthesis of enantio-enriched BINOL derivatives.

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Institution:
University of Oxford
Oxford college:
St Cross College
Role:
Author

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Supervisor
Engineering & Physical Sciences Research Council More from this funder
Type of award:
DPhil
Level of award:
Doctoral
Awarding institution:
University of Oxford
UUID:
uuid:3e7cb2c5-5f8e-406e-89b0-fc873e552dad
Deposit date:
2017-05-30

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