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

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

doi:10.1021/jacs.1c01242

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

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

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

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.

Original language	English (US)
Pages (from-to)	4921-4927
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	143
Issue number	13
DOIs	https://doi.org/10.1021/jacs.1c01242
State	Published - Apr 7 2021

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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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.",

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note = "Funding Information: Funding was received from the Welch Foundation (I-1612) and the NIH (R01 CA216863 J.M.R; T32GM127216 C.R.D.). Publisher Copyright: {\textcopyright} ",

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AU - Luvaga, Irungu K.

AU - Ready, Joseph M.

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AB - 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.

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

Abstract

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