P -Chiral Phosphine Sulfide Synthesis by Combination of Enzymatic Desymmetrization and Successive Deformylative P-C Cross-Couplings

A process for the synthesis of P-chiral triarylphosphine sulfides via sequential Pd-catalyzed stereospecific P-C coupling reactions of P-chiral precursors prepared by enzymatic desymmetrization was developed. Three independent aryl substituents could be introduced onto the P atom by the sequential P...

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Bibliographic Details
Published inSynlett Vol. 33; no. 15; pp. 1511 - 1514
Main Authors Ohta, Hidetoshi, Nakashima, Yoshiki, Kayahara, Kento, Hashimoto, Naoki, Tanaka, Ippei, Tadokoro, Tomoki, Watanabe, Yutaka, Hayashi, Minoru
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 16.09.2022
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ROUTE
HYDROGENATION
RHODIUM
ENANTIOSELECTIVE SYNTHESIS
LIGANDS
phosphine sulfide
palladium
enzymatic desymmetrization
EFFICIENT ASYMMETRIC-SYNTHESIS
OXIDES
P-chiral phosphine
P-C coupling
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Summary:A process for the synthesis of P-chiral triarylphosphine sulfides via sequential Pd-catalyzed stereospecific P-C coupling reactions of P-chiral precursors prepared by enzymatic desymmetrization was developed. Three independent aryl substituents could be introduced onto the P atom by the sequential P-C couplings under mild conditions while retaining the high enantiopurity.
ISSN:0936-5214
1437-2096
DOI:10.1055/a-1873-3530