Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji-Trost Allylation

Matteo Faltracco, Silvia Cotogno, Christophe M.L. Vande Velde, Eelco Ruijter

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

We report the intramolecular Tsuji-Trost reaction of Ugi adducts to give spiro-diketopiperazines in high yield and with high enantioselectivity. This approach allows the catalytic asymmetric construction of a broad range of these medicinally important heterocycles under mild conditions, in two steps from cheap, commercially available starting materials.

Original languageEnglish
Pages (from-to)12058-12070
Number of pages13
JournalThe Journal of organic chemistry
Volume84
Issue number18
Early online date26 Aug 2019
DOIs
Publication statusPublished - 20 Sep 2019

Fingerprint

Diketopiperazines
Allylation
Enantioselectivity

Cite this

@article{ade05c2696ef4406a9134f000fe5f80a,
title = "Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji-Trost Allylation",
abstract = "We report the intramolecular Tsuji-Trost reaction of Ugi adducts to give spiro-diketopiperazines in high yield and with high enantioselectivity. This approach allows the catalytic asymmetric construction of a broad range of these medicinally important heterocycles under mild conditions, in two steps from cheap, commercially available starting materials.",
author = "Matteo Faltracco and Silvia Cotogno and {Vande Velde}, {Christophe M.L.} and Eelco Ruijter",
year = "2019",
month = "9",
day = "20",
doi = "10.1021/acs.joc.9b01994",
language = "English",
volume = "84",
pages = "12058--12070",
journal = "The Journal of organic chemistry",
issn = "1520-6904",
publisher = "American Chemical Society",
number = "18",

}

Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji-Trost Allylation. / Faltracco, Matteo; Cotogno, Silvia; Vande Velde, Christophe M.L.; Ruijter, Eelco.

In: The Journal of organic chemistry, Vol. 84, No. 18, 20.09.2019, p. 12058-12070.

Research output: Contribution to JournalArticleAcademicpeer-review

TY - JOUR

T1 - Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji-Trost Allylation

AU - Faltracco, Matteo

AU - Cotogno, Silvia

AU - Vande Velde, Christophe M.L.

AU - Ruijter, Eelco

PY - 2019/9/20

Y1 - 2019/9/20

N2 - We report the intramolecular Tsuji-Trost reaction of Ugi adducts to give spiro-diketopiperazines in high yield and with high enantioselectivity. This approach allows the catalytic asymmetric construction of a broad range of these medicinally important heterocycles under mild conditions, in two steps from cheap, commercially available starting materials.

AB - We report the intramolecular Tsuji-Trost reaction of Ugi adducts to give spiro-diketopiperazines in high yield and with high enantioselectivity. This approach allows the catalytic asymmetric construction of a broad range of these medicinally important heterocycles under mild conditions, in two steps from cheap, commercially available starting materials.

UR - http://www.scopus.com/inward/record.url?scp=85072508808&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85072508808&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.9b01994

DO - 10.1021/acs.joc.9b01994

M3 - Article

VL - 84

SP - 12058

EP - 12070

JO - The Journal of organic chemistry

JF - The Journal of organic chemistry

SN - 1520-6904

IS - 18

ER -