Diastereoselective Synthesis of Z‐Alkenyl Disulfides from α‐Thiophosphorylated Ketones and Thiosulfonates

We developed a simple and efficient method for the synthesis of functionalized unsymmetrical Z‐alkenyl disulfides under mild conditions in moderate to good yields. The designed method is based on the reaction of α‐thiophosphorylated carbonyl compounds with thiotosylates in the presence of a base. Th...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 362; no. 3; pp. 618 - 626
Main Authors Musiejuk, Mateusz, Doroszuk, Justyna, Jędrzejewski, Bartosz, Ortiz Nieto, Gregory, Marin Navarro, Marisol, Witt, Dariusz
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 06.02.2020
Wiley Subscription Services, Inc
Subjects
alkenes
Carbonyl compounds
Carbonyls
Chemistry
Chemistry, Applied
Chemistry, Organic
diastereoselectivity
Disulfides
Ketones
phosphorodithioic acid
Physical Sciences
Science & Technology
Stereoselectivity
Synthesis
thiotosylates
CONVENIENT SYNTHESIS
Disulfides
EFFICIENT SYNTHESIS
thiotosylates
SULFENYLATION
diastereoselectivity
TETRATHIOMOLYBDATE
alkenes
Z-AJOENE
THIOLS
VERSATILE
phosphorodithioic acid
UNSYMMETRICAL DISULFIDES
CHEMISTRY
DERIVATIVES
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Summary:We developed a simple and efficient method for the synthesis of functionalized unsymmetrical Z‐alkenyl disulfides under mild conditions in moderate to good yields. The designed method is based on the reaction of α‐thiophosphorylated carbonyl compounds with thiotosylates in the presence of a base. The developed method allows the preparation of unsymmetrical Z‐alkenyl disulfides bearing additional hydroxy, carboxy, or ester functionalities
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201901208