Synlett 2016; 27(09): 1423-1427
DOI: 10.1055/s-0035-1561573
letter
© Georg Thieme Verlag Stuttgart · New York

An Efficient Protecting-Group-Free Synthesis of Vinylic Sulfoximines via Horner–Wadsworth–Emmons Reaction

Praveen K. Chinthakindi
a   Catalysis and Peptide Research Unit, University of KwaZulu-Natal, Durban 4000, South Africa, eMail: Naickert1@ukzn.ac.za
,
Ganesh Chandra Nandi
a   Catalysis and Peptide Research Unit, University of KwaZulu-Natal, Durban 4000, South Africa, eMail: Naickert1@ukzn.ac.za
c   Organic Chemistry Section, CSIR-National Institute for Interdisciplinary Science and Technology, Trivandrum 695019, India
,
Thavendran Govender
a   Catalysis and Peptide Research Unit, University of KwaZulu-Natal, Durban 4000, South Africa, eMail: Naickert1@ukzn.ac.za
,
Hendrik G. Kruger
a   Catalysis and Peptide Research Unit, University of KwaZulu-Natal, Durban 4000, South Africa, eMail: Naickert1@ukzn.ac.za
,
Tricia Naicker*
a   Catalysis and Peptide Research Unit, University of KwaZulu-Natal, Durban 4000, South Africa, eMail: Naickert1@ukzn.ac.za
,
Per I. Arvidsson*
a   Catalysis and Peptide Research Unit, University of KwaZulu-Natal, Durban 4000, South Africa, eMail: Naickert1@ukzn.ac.za
b   Science for Life Laboratory, Drug Discovery & Development Platform & Division of Translational Medicine and Chemical Biology, Department of Medical Biochemistry and Biophysics, Karolinska Institutet, S-171 21 Solna, Sweden   eMail: per.arvidsson@scilifelab.se
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Publikationsverlauf

Received: 05. Dezember 2015

Accepted after revision: 20. Januar 2016

Publikationsdatum:
24. Februar 2016 (online)


Abstract

Herein, we report a convenient synthesis of aryl-substituted (E)-vinylic NH-sulfoximines via the Horner–Wadsworth–Emmons reaction without the use of protection–deprotection group strategies.

Supporting Information

 
  • References and Notes

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  • 17 General Procedure for the Synthesis of Compounds 7a–f and 8a,b n-BuLi (1.2 equiv of 1.6 M solution in hexane) was added to a solution of diethylphenylsulfonimidoylmethylphosphonate (1.0 equiv) in dry THF (4 mL) kept at –78 °C. The reaction was stirred for 1 h before sequential addition of aldehyde (1.3 equiv). Then the resulting reaction mixture was stirred at –78 °C for 1 h. After completion, the reaction mixture was neutralized with NH4Cl and extracted with EtOAc (3 × 20 mL) to give the title product. (E)-[2-(Phenylsulfonimidoyl)vinyl]benzene (7a) 1HNMR (400 MHz, CDCl3): δ = 8.03–8.01 (2 H, m, ArH), 7.63 (1 H, d, J = 15.2 Hz), 7.58–7.48 (3 H, m, ArH), 7.46–7.44 (2 H, m, ArH), 7.36–7.33 (3 H, m, ArH), 6.96 [1 H, d, J = 15.2 Hz, (E)-CH=CH]. 13C NMR (100 MHz, CDCl3): δ = 142.8, 141.7, 132.8, 132.6, 130.9, 130.0, 129.4, 129.3, 129.0, 128.5, 128.3 (2), 127.9 (2). IR (ATR): ν = 3262, 3059, 1703, 1614, 1575, 1215, 1070, 744, 709, 607 cm–1. HRMS (ESI+): m/z [M + H]+ calcd for C14H13NOSH+: 244.0791; found: 244.0811 [M + H]+.
  • 18 General Procedure for the Synthesis of Compound 7g n-BuLi (1.2 equiv of 1.6 M solution in hexane) was added to a solution of diethylphenylsulfonimidoylmethylphosphonate (1.0 equiv) in dry THF (4 mL) kept at –78 °C. The reaction was stirred for 1 h before sequential addition of acetophenone (1.3 equiv). Then the resulting reaction mixture was stirred at r.t. for 1 h. The reaction mixture was then neutralized with aq NH4Cl and extracted with EtOAc (3 × 20 mL) to give the title product after workup. (E)-(2-Phenylprop-1-enylsulfonimidoyl)benzene (7g) 1H NMR (400 MHz, CDCl3): δ = 8.06–8.04 (2 H, m, ArH), 7.63–7.53 (4 H, m, ArH), 7.44–7.42 (2 H, m, ArH), 7.38–7.33 (2 H, m, ArH), 6.89 (1 H, s, CH=C), 2.44 (3H , d, J = 1 Hz, CH=CCH 3). 13C NMR (100 MHz, CDCl3): δ = 139.9, 133.4, 130.2, 129.5 (3 C), 128.9 (3 C), 128.0 (3 C), 126.5 (2 C), 16.9. IR (ATR): ν = 2958, 2920, 2849, 2171, 2018, 1456, 1123, 1049, 623, 499 cm–1. HRMS (ESI+): m/z [M + H]+ calcd for for C15H15NOSH+: 258.0947; found: 258.0967 [M + H]+.
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