Synthesis of Soai aldehydes for asymmetric autocatalysis by desulfurative cross-coupling

Oleg V. Maltsev; Alexander Pöthig; Lukas Hintermann

doi:10.1021/ol500189s

Synthesis of Soai aldehydes for asymmetric autocatalysis by desulfurative cross-coupling

Oleg V. Maltsev
, Alexander Pöthig
, Lukas Hintermann

Associate Professorship of Organic Chemistry

Technical University of Munich

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

35 Scopus citations

Abstract

Palladium-catalyzed dehydrosulfurative Liebeskind-Srogl coupling of terminal alkynes with 2-mercapto-1,3-pyrimidine-5-carbaldehyde under base-free conditions provides 2-(alkynyl)-1,3-pyrimidine-5-carbaldehydes, which are substrates for autocatalytic amplification of chirality according to Soai et al. The mercapto aldehyde acceptor is obtained by condensation of Arnold's vinamidinium salt with thiourea.

Original language	English
Pages (from-to)	1282-1285
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	5
DOIs	https://doi.org/10.1021/ol500189s
State	Published - 7 Mar 2014

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title = "Synthesis of Soai aldehydes for asymmetric autocatalysis by desulfurative cross-coupling",

abstract = "Palladium-catalyzed dehydrosulfurative Liebeskind-Srogl coupling of terminal alkynes with 2-mercapto-1,3-pyrimidine-5-carbaldehyde under base-free conditions provides 2-(alkynyl)-1,3-pyrimidine-5-carbaldehydes, which are substrates for autocatalytic amplification of chirality according to Soai et al. The mercapto aldehyde acceptor is obtained by condensation of Arnold's vinamidinium salt with thiourea.",

author = "Maltsev, \{Oleg V.\} and Alexander P{\"o}thig and Lukas Hintermann",

year = "2014",

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volume = "16",

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journal = "Organic Letters",

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T1 - Synthesis of Soai aldehydes for asymmetric autocatalysis by desulfurative cross-coupling

AU - Maltsev, Oleg V.

AU - Pöthig, Alexander

AU - Hintermann, Lukas

PY - 2014/3/7

Y1 - 2014/3/7

N2 - Palladium-catalyzed dehydrosulfurative Liebeskind-Srogl coupling of terminal alkynes with 2-mercapto-1,3-pyrimidine-5-carbaldehyde under base-free conditions provides 2-(alkynyl)-1,3-pyrimidine-5-carbaldehydes, which are substrates for autocatalytic amplification of chirality according to Soai et al. The mercapto aldehyde acceptor is obtained by condensation of Arnold's vinamidinium salt with thiourea.

AB - Palladium-catalyzed dehydrosulfurative Liebeskind-Srogl coupling of terminal alkynes with 2-mercapto-1,3-pyrimidine-5-carbaldehyde under base-free conditions provides 2-(alkynyl)-1,3-pyrimidine-5-carbaldehydes, which are substrates for autocatalytic amplification of chirality according to Soai et al. The mercapto aldehyde acceptor is obtained by condensation of Arnold's vinamidinium salt with thiourea.

UR - https://www.scopus.com/pages/publications/84896760057

U2 - 10.1021/ol500189s

DO - 10.1021/ol500189s

M3 - Article

AN - SCOPUS:84896760057

SN - 1523-7060

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SP - 1282

EP - 1285

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

Synthesis of Soai aldehydes for asymmetric autocatalysis by desulfurative cross-coupling

Abstract

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