Enantioselektive Katalysatoren zur Synthese von α‐substituierten Allylboronsäureestern – ein effizienter Zugang zu isomerenreinen Homoallylalkoholen

(E)‐δ‐Boryl‐substituted anti‐homoallylic alcohols are synthesized in a highly diastereo‐ and enantioselective manner from 1,1‐di(boryl)alk‐3‐enes and aldehydes. Mechanistically, the reaction consists of 1) palladium‐catalyzed double‐bond transposition of the 1,1‐di(boryl)alk‐3‐enes to 1,1‐di(boryl)alk‐2‐enes, 2) chiral phosphoric acid catalyzed allylation of aldehydes, and 3) palladium‐catalyzed geometrical isomerization from the Z to E isomer. As a result, the configurations of two chiral centers and one double bond are all controlled with high selectivity in a single reaction vessel.

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Enantioselective Synthesis of (E)‐δ‐Boryl‐Substituted anti‐Homoallylic Alcohols Using Palladium and a Chiral Phosphoric Acid

Miura

Nakahashi

Murakami

2017

Angewandte Chemie

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Alternating Radical Stabilities: A Convergent Route to Terminal and Internal Boronates

Zard

Huang²,

Michalland³

2019

Angewandte Chemie

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Pinacolato boronates (Bpin) with an empty p-orbital on boron stabilizea na djacent carbon radical, in contrast to diethanolamino boronates [B(DEA)] where the boron is sp 3hybridized. By alternately placing apinacol or diethanolamine moiety on the boron atom, thus stabilizing or not stabilizing the corresponding adjacent radical, it is possible to control the behavior of a-boronyl xanthates and construct al arge variety of terminal or internal boronates in am odular fashion. The remarkable tolerance of polar groups and the ability to introduce quaternary centers are particularly noteworthy features of this process.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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Enantioselective Synthesis of (E)‐δ‐Boryl‐Substituted anti‐Homoallylic Alcohols Using Palladium and a Chiral Phosphoric Acid

2017

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(E)-δ-Boryl-substituted anti-homoallylic alcohols are synthesized in a highly diastereo- and enantioselective manner from 1,1-di(boryl)alk-3-enes and aldehydes. Mechanistically, the reaction consists of 1) palladium-catalyzed double-bond transposition of the 1,1-di(boryl)alk-3-enes to 1,1-di(boryl)alk-2-enes, 2) chiral phosphoric acid catalyzed allylation of aldehydes, and 3) palladium-catalyzed geometrical isomerization from the Z to E isomer. As a result, the configurations of two chiral centers and one double bond are all controlled with high selectivity in a single reaction vessel.

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Enantioselektive Katalysatoren zur Synthese von α‐substituierten Allylboronsäureestern – ein effizienter Zugang zu isomerenreinen Homoallylalkoholen

Cited by 9 publications

References 45 publications

Enantioselective Synthesis of (E)‐δ‐Boryl‐Substituted anti‐Homoallylic Alcohols Using Palladium and a Chiral Phosphoric Acid

Enantioselective Synthesis of (E)‐δ‐Boryl‐Substituted anti‐Homoallylic Alcohols Using Palladium and a Chiral Phosphoric Acid

Alternating Radical Stabilities: A Convergent Route to Terminal and Internal Boronates

Enantioselective Synthesis of (E)‐δ‐Boryl‐Substituted anti‐Homoallylic Alcohols Using Palladium and a Chiral Phosphoric Acid

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