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

Davis, Colton R; Luvaga, Irungu K; Ready, Joseph M

Davis, Colton R; Luvaga, Irungu K; Ready, Joseph M.

Afiliação

Davis CR; Department of Biochemistry, UT Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390-8548, United States.
Luvaga IK; Department of Biochemistry, UT Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390-8548, United States.
Ready JM; Department of Biochemistry, UT Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390-8548, United States.

J Am Chem Soc ; 143(13): 4921-4927, 2021 04 07.

Article em En | MEDLINE | ID: mdl-33755457

ABSTRACT

ABSTRACT

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.

Assuntos

Compostos Alílicos/química; Ácidos Borônicos/química; Metais/química; Catálise; Estereoisomerismo

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Ácidos Borônicos / Compostos Alílicos / Metais Idioma: En Revista: J Am Chem Soc Ano de publicação: 2021 Tipo de documento: Article

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