Unknown

Dataset Information

0

Merging Asymmetric [1,2]-Additions of Lithium Acetylides to Carbonyls with Type II Anion Relay Chemistry.


ABSTRACT: An enantioselective three-component coupling reaction has been developed, enabling the union of a variety of lithium acetylides and electrophiles exploiting an achiral linchpin via an anionic reaction cascade. This Type II Anion Relay Chemistry tactic is initiated via an enantioselective [1,2]-carbonyl addition exploiting BINOL catalysis to access an enantioenriched alkoxide intermediate. Migration of charge across the linchpin via a [1,4]-Brook rearrangement with electrophile capture affords a three-component propargyl ether adduct. Herein, we report the development, scope, and limitations of this reaction sequence.

SUBMITTER: O'Brien KT 

PROVIDER: S-EPMC7307215 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

altmetric image

Publications

Merging Asymmetric [1,2]-Additions of Lithium Acetylides to Carbonyls with Type II Anion Relay Chemistry.

O'Brien Kevin T KT   Smith Amos B AB  

Organic letters 20190909 18


An enantioselective three-component coupling reaction has been developed, enabling the union of a variety of lithium acetylides and electrophiles exploiting an achiral linchpin via an anionic reaction cascade. This Type II Anion Relay Chemistry tactic is initiated via an enantioselective [1,2]-carbonyl addition exploiting BINOL catalysis to access an enantioenriched alkoxide intermediate. Migration of charge across the linchpin via a [1,4]-Brook rearrangement with electrophile capture affords a  ...[more]

Similar Datasets

| S-EPMC4285137 | biostudies-literature
| S-EPMC11322804 | biostudies-literature
| S-EPMC3528832 | biostudies-literature
| S-EPMC4633699 | biostudies-literature
| S-EPMC3985715 | biostudies-literature
| S-EPMC3969824 | biostudies-literature
| S-EPMC5712993 | biostudies-literature
| S-EPMC3135908 | biostudies-other
| S-EPMC5558205 | biostudies-literature
| S-EPMC5910188 | biostudies-literature