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Please login to access the full content or check if you have access via24.4.3.5.4.2.1 Method 1: Oxidation of 1-(Vinylsulfanyl)alk-1-ynes
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Ulfkjær, A.; Pittelkow, M., Science of Synthesis Knowledge Updates, (2018) 1, 198.
1-(Vinylsulfanyl)alk-1-ynes 143 (see Section 24.4.3.5.4.1.2 for synthesis) can be oxidized with an excess amount of 3-chloroperoxybenzoic acid to give the corresponding sulfones 144 (Scheme 108).[71] Subsequent reaction of the sulfone through a regiospecific gold-catalyzed desulfonylative double oxidation gives 1,2-diketones, e.g. 145 in 75% yield, using the N-heterocyclic carbene based [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene][bis(trifluoromethanesulfonyl)amido]gold(I) {[Au(IPr)(NTf2)]} catalyst in the presence of 2,6-dichloropyridine N-oxide. Upon applying similar reaction conditions to 2-methylprop-1-enyl 2-phenylethynyl sulfone, trans-dienone 146 is produced instead of the expected diketone. In a similar manner, cyclohex-1-enyl 2-phenylethynyl sulfone yields dienone 147 as two diastereomers, together with bicyclic furan 148; the latter is formed through 4π-electrocyclic ring closure.
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| M8 | M8 | M8 | Meeeee (%) | Mee |
|---|---|---|---|---|
| M | Me | M | 88 | [88] |
| M | Me | Me | 88 | [88] |
| (MM8)8 | M | 88 | [88] | |
e Meeee ee 888 eeeeeeee eeee eeeeeeeeeeeeeee (eee Meeeee 888, Meeeeee 88.8.8.8.8.8.8 eee eeeeeee)
Meeeeeeeeeee Meeeeeeee
Meeeeee Meeeeeeeeeeee Meeeeeee 888; Meeeeee Meeeeeeee:[88]
MMMMM (8.88 eeeee) eee eeeee ee e eeee ee eee eeeeeee 888 (8 eeee) ee MM8Me8 (88 eM) eeeeee ee 8 °M. Mee eeeeeee eee eeeeeee ee eee eeee eeeeeeeeeee eee 8 e eee eeee ee ee eee 88 e. Mee eeeeeee eee eeee eeeeee eeee eee. ee MeMMM8, eeeee (MeMM8), eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe) ee eeeeee eee eeeee eeeeeeee.
(8M)-8,8-Meeeeeeeeee-8-eee-8,8-eeeee (888); Meeeeee Meeeeeeee:[88]
M 8-eeee eeee eee eeeeeee eeee MeMM8 (8 eM), 8-Å eeeeeeeee eeeeee (888 ee), (M)-8-eeeeee-8-[(8-eeeeeeeeeee)eeeeeeee]eeeeeeeee (8.88 eeee), eee 8,8-eeeeeeeeeeeeeeee M-eeeee (88 ee, 8.8 eeee). Mee eeeeeee eee eeeeeee ee ee eee 88 eee. [Me(MMe)(MMe8)] (88.8 ee, 8.8888 eeee) eee eeee eeeee, eee eee eeeeeee eee eeeeeee ee 88 °M eee 88 e. Meee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 888:8) ee eeee eee eeeee eeeeeeee; eeeee: 88%.
References
| [71] | Meee, M.; Meeee, M., Meeee. Meee. Mee. Me., (8888) 88, 88 888. |
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