SCOPUS 정보 검색 플랫폼

Volumn , Issue 13, 2008, Pages 2051-2055

The synthesis of N-TBS-S-alkynyl sulfoximines

Author keywords

Alkyne; H nig's base; Sulfoximine; Triflic anhydride

Indexed keywords

ALKYNYL GROUP; SULFONE DERIVATIVE; SULFOXIMINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 49749144187 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1077956 Document Type: Article

Times cited : (5)

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26
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- General Experimental Procedures: To a solution of DIPEA (2.5 mmol) in THF (10 mL) at 0 °C, was added BuLi (2.5 mmol) with stirring. After 10 min, the solution was cooled to -78 °C, and slowly added to a flask that contained 9 (2 mmol) in THF (10 mL) at -78 °C. The solution was warmed to r.t. for 15 min, then was cooled back to -78 °C. Ester was added (10 mmol) and the solution was warmed to r.t. and then refluxed for 8 h. After TLC showed no starting material, the solution was quenched by sat. NH 4Cl (10 mL, and extracted with Et2O (3 × 10 mL, The combined organic phases were washed with brine (10 mL, and dried with Na2SO4. Removal of solvent and chromatographic purification afforded keto sulfoximines 10. Procedure A: To 10 (1 mmol) in toluene (5 mL) at r.t. was slowly added DIPEA (6.0 equiv, followed by triflate anhydride 2.3 equiv, The solution was refluxed until TLC showed no starting
- 4 and concentrated in vacuo to give a colorless oil. The oil was purified by chromatography, eluting with 20% EtOAc in hexane, to give the pure final product.

27
- 49749119682
- Data on selected compounds: 10a: oil. 1H NMR (500 MHz, CDCl3, δ, 7.85-7.92 (m, 4 H, 7.38-7.54 (m, 6 H, 4.70 (d, J, 12.6 Hz, 1 H, 4.54 (d, J, 12.6 Hz, 1 H, 0.83 (s, 9 H, 0.01 (d, J, 10.5 Hz, 6 H, 13C NMR (125.8 MHz, CDCl 3, δ, 189.1, 143.5, 136.5, 133.6, 132.6, 129.5, 128.7, 128.5, 127.9, 67.8, 25.8, 20.7, 17.9, 2.6, 2.6. IR (CH2Cl2, 3064, 2949, 2921, 2855, 1679, 1446, 1274, 1160, 829 cm-1. HRMS: m/z calcd for C20H27NO2SSiNa, 396.1429; found: 396.1315.10b: oil. 1H NMR (500 MHz, CDCl3, δ, 7.80-7.82 (m, 2 H, 7.26-7.50 (m, 7 H, 4.80 (d, J= 13.0 Hz, 1 H, 4.72 (d, J= 13.0 Hz, 1 H, 0.86 (s, 9 H, 0.01-0.30 (s, 6 H, 13C NMR 125.8 MHz, CDCl3, δ, 191.0, 143.0, 137.8, 132.5, 132.4, 131.4, 130.8, 130.4, 128.6, 127.8, 126.8, 70.8
- 1.

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