Regio- and stereocontrolled access to γ-boronated unsaturated amino esters and derivatives from (Z)-alkenyl 1,2-bis(boronates).

Tailor Sridhar; Fabienne Berrée; Gangavaram V M Sharma; Bertrand Carboni

doi:10.1021/jo402237t

Journal articles

Regio- and stereocontrolled access to γ-boronated unsaturated amino esters and derivatives from (Z)-alkenyl 1,2-bis(boronates).

Tailor Sridhar ¹ Fabienne Berrée ² Gangavaram V M Sharma ^{1, *} Bertrand Carboni ^{2, *}

* Corresponding author

1 Organic and Biomolecular Chemistry Division

IICT - CSIR Indian Institute of Chemical Technology

2 ISCR - Institut des Sciences Chimiques de Rennes

Abstract : The Borono-Mannich reaction of (Z)-1-alkene-1,2-diboronic esters proceeded regioselectively at the terminal C-B bond to afford (E)-γ-boronated unsaturated amino esters in good yields. These compounds were then subjected to Suzuki couplings for the creation of diversely substituted olefinic amino acid systems. Several other functional transformations were also carried out to illustrate the synthetic utility of the Petasis products.

Keywords : Suzuki couplings Petasis Aminoesters boronic esters

Document type :

Journal articles

Domain :

Chemical Sciences / Organic chemistry

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https://hal-univ-rennes1.archives-ouvertes.fr/hal-00955530
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Submitted on : Tuesday, March 4, 2014 - 4:08:54 PM
Last modification on : Thursday, March 5, 2020 - 2:05:19 PM

Regio- and stereocontrolled access to γ-boronated unsaturated amino esters and derivatives from (Z)-alkenyl 1,2-bis(boronates).

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Regio- and stereocontrolled access to γ-boronated unsaturated amino esters and derivatives from (Z)-alkenyl 1,2-bis(boronates).

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