Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol

Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol

Alkenyl boronates add to Ir­(π-allyl) intermediates with high enantioselectivity. A 1,2-metalate shift forms a second C–C bond and sets a 1,3-stereochemical relationship. The three-component coupling provides tertiary boronic esters that can undergo multiple additional functionalizations. An extensi...

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Veröffentlicht in:Journal of the American Chemical Society 2021-04, Vol.143 (13), p.4921-4927
Hauptverfasser: Davis, Colton R, Luvaga, Irungu K, Ready, Joseph M
Format: Artikel
Sprache:eng
Schlagworte:
Allyl Compounds - chemistry
Boronic Acids - chemistry
Catalysis
Metals - chemistry
Stereoisomerism
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Zusammenfassung:Alkenyl boronates add to Ir­(π-allyl) intermediates with high enantioselectivity. A 1,2-metalate shift forms a second C–C bond and sets a 1,3-stereochemical relationship. The three-component coupling provides tertiary boronic esters that can undergo multiple additional functionalizations. An extension to trisubstituted olefins sets three contiguous stereocenters.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.1c01242