Stereoselective Decarboxylative Alkylation of Titanium(IV) Enolates with Diacyl Peroxides

Alejandro Gómez-Palomino; Marina Pérez-Palau; Pedro Romea; Fèlix Urpí; Marc Del Olmo; Timo Hesse; Sonja Fleckenstein; Enrique Gómez-Bengoa; Lia Sotorríos; Mercè Font-Bardía

doi:10.1021/acs.orglett.9b04148

Stereoselective Decarboxylative Alkylation of Titanium(IV) Enolates with Diacyl Peroxides

Alejandro Gómez-Palomino, Marina Pérez-Palau, Pedro Romea, Fèlix Urpí, Marc Del Olmo, Timo Hesse, Sonja Fleckenstein, Enrique Gómez-Bengoa, Lia Sotorríos, Mercè Font-Bardía

Pharmacy

Universitat de Barcelona

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

Abstract

Simple treatment of chiral titanium(IV) enolates with diacyl peroxides produces highly diastereoselective decarboxylative alkylations to efficiently deliver the corresponding adducts, most of which are not accessible through any of the current alkylating procedures. Such an unprecedented alkylation proceeds through an SET process that triggers the decomposition of the peroxide into a carbon-centered radical that finally combines with the resulting Cα radical. The procedure has been applied to the enantioselective synthesis of arundic acid.

Original language	English
Pages (from-to)	199–203
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	1
Early online date	11 Dec 2019
DOIs	https://doi.org/10.1021/acs.orglett.9b04148
Publication status	Published - 3 Jan 2020

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title = "Stereoselective Decarboxylative Alkylation of Titanium(IV) Enolates with Diacyl Peroxides",

abstract = "Simple treatment of chiral titanium(IV) enolates with diacyl peroxides produces highly diastereoselective decarboxylative alkylations to efficiently deliver the corresponding adducts, most of which are not accessible through any of the current alkylating procedures. Such an unprecedented alkylation proceeds through an SET process that triggers the decomposition of the peroxide into a carbon-centered radical that finally combines with the resulting Cα radical. The procedure has been applied to the enantioselective synthesis of arundic acid.",

author = "Alejandro G{\'o}mez-Palomino and Marina P{\'e}rez-Palau and Pedro Romea and F{\`e}lix Urp{\'i} and {Del Olmo}, Marc and Timo Hesse and Sonja Fleckenstein and Enrique G{\'o}mez-Bengoa and Lia Sotorr{\'i}os and Merc{\`e} Font-Bard{\'i}a",

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doi = "10.1021/acs.orglett.9b04148",

language = "English",

volume = "22",

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journal = "Organic Letters",

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T1 - Stereoselective Decarboxylative Alkylation of Titanium(IV) Enolates with Diacyl Peroxides

AU - Gómez-Palomino, Alejandro

AU - Pérez-Palau, Marina

AU - Romea, Pedro

AU - Urpí, Fèlix

AU - Del Olmo, Marc

AU - Hesse, Timo

AU - Fleckenstein, Sonja

AU - Gómez-Bengoa, Enrique

AU - Sotorríos, Lia

AU - Font-Bardía, Mercè

PY - 2020/1/3

Y1 - 2020/1/3

N2 - Simple treatment of chiral titanium(IV) enolates with diacyl peroxides produces highly diastereoselective decarboxylative alkylations to efficiently deliver the corresponding adducts, most of which are not accessible through any of the current alkylating procedures. Such an unprecedented alkylation proceeds through an SET process that triggers the decomposition of the peroxide into a carbon-centered radical that finally combines with the resulting Cα radical. The procedure has been applied to the enantioselective synthesis of arundic acid.

AB - Simple treatment of chiral titanium(IV) enolates with diacyl peroxides produces highly diastereoselective decarboxylative alkylations to efficiently deliver the corresponding adducts, most of which are not accessible through any of the current alkylating procedures. Such an unprecedented alkylation proceeds through an SET process that triggers the decomposition of the peroxide into a carbon-centered radical that finally combines with the resulting Cα radical. The procedure has been applied to the enantioselective synthesis of arundic acid.

UR - http://europepmc.org/abstract/med/31825223

U2 - 10.1021/acs.orglett.9b04148

DO - 10.1021/acs.orglett.9b04148

M3 - Letter

C2 - 31825223

SN - 1523-7052

VL - 22

SP - 199

EP - 203

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

Stereoselective Decarboxylative Alkylation of Titanium(IV) Enolates with Diacyl Peroxides

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