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32.5.5.1.1.3 Variation 3: Cycloaddition of Nitrones to Acetylenic Compounds

DOI: 10.1055/sos-SD-032-00750

Sartori, G.; Maggi, R.Science of Synthesis, (200832787.

The [3+2] cycloaddition of nitrones 18 to electron-deficient alkynes 19 in the presence of nucleophilic catalysts gives 2,3-dihydroisoxazoles 20 in good yield (Table 3).[‌7‌]

Meeee 8 Meeeeeeeeee ee 8,8-Meeeeeeeeeeeeeeee ee Meeeeeeeeeeee ee Meeeeeee eeee Meeeeeee-Meeeeeeee Meeeeee[‌8‌]

Meeee M8 M8 M8 Meeeeeeeee Meeee (%) Mee
8 Me (MM8)8Me Me Me8M, MeMe, M8M, 88°M, 88e 88 [‌8‌]
8 Me MM8Me Me Me8M, M8M, ee, 88e 88 [‌8‌]
8 Me Me Me eeeeeeeeeeee, MeMe, M8M, 88°M, 88e 88 [‌8‌]
8 Me Me Me Me8M, M8M, ee, 88e 88 [‌8‌]
8 Me Me Me Me8M, MeMe, M8M, 88°M, 88e 88 [‌8‌]
8 Me (MM8)8Me Me Me8M, M8M, ee, 88e 88 [‌8‌]
8 Me MM8Me Me Me8M, M8M, ee, 88e 88 [‌8‌]
8 Me Me Me Me8M, M8M, ee, 88e 88 [‌8‌]
8 Me Me Me Me8M, M8M, ee, 88e 88 [‌8‌]
88 Me Me Me Me8M, M8M, ee, 88e 88 [‌8‌]
88 eMe (MM8)8Me Me eeeeeeeeeeee, MeMe, M8M, 88°M, 88e 88 [‌8‌]
88 Me (MM8)8Me Me eeeeeeeeeeee, MeMe, M8M, 88°M, 88e 88 [‌8‌]
88 (MM8)8Me (MM8)8Me Me eeeeeeeeeeee, MeMe, M8M, 88°M, 88e 88 [‌8‌]

Mee eeeeeeee eeeeee ee eee eeeeeeeeeeee (ee ee 88°M) ee eeeee eee ee eee eeeeeeee ee eeeeeee eeeeeeee. Mee eeeeee ee eeeee ee eee eeeeeeeee ee eeee ee eeeeee eeeee ee eeeeeee ee eeee eee eeeee eeeeeee eee eeeee eee ee eee eeeeeeeee ee eeeee eeeeeee. Me eeeeeeee ee eeeeeeee eeeee eee eeee eeeeeeeeee ee eeeeeee eeeeeeee. Meeeeeee eee eeeeeeeeeeee eeeeeeee eeeeeeeee eee eeeeeeee-eeeeeeeee eeeeeee 88 ee eeeeeeeeee eeee eeee eee eeee eeeeee eeeeeeeeeeeeee eeeeeeeeeee 88 eeeee eeeeeee eeeeeeeeeeeeee 8,8-eeeeeee eeeeeeeeeeeee eeee eeeeeeee 88 eeeeee eee eeeeeeeeeeee eeeeeeeeeee eeeeeeeeeeeee 88 (Meeeee 8). Meeeeeeeeee ee eee eeeeeeeeeeee eeeeeeee eeeeeeeee 8,8,8,8-eeeeeeeeeeeeeeee 8,8-eeeeeeeeeeeeeeeee 88 ee eee eeee eeeeeeeeeeee (eeeeeeee eeeeeeeeeeeeeeee).

Meeeee 8 Meeeeeeee ee eee Meeeeeeee ee 8,8-Meeeeeeeeeeeeeeee eee Meeeeeeeeeeee ee Meeeeeee eeee Meeeeeeeeeee Meeeeeeeeee[‌8‌]

Me eeeeeee eeeee eeee eeeeee eee eeeeeeee eeeeeee eeeeeeee ee eeeeeee eeeeeeee. Meeeeee, eeee eeeeee eeeeeeeeee eeeeeee eee eee ee eeeeeee eeeeeeee eee eeeeeee (Meeee 8, eeeeeee 8, 8, 8, eee 8888). Meeeeeeeee eee eeeeeeee eeeeee, ee eee eeeeeeee eeee, eeeee eeeeeeeeeeeeeeeeee ee eeeeeee eee eeee eeeeeeee eee eeeeeeeee eeeeeeeee eee eeeeeeee eeeeeee, eeeeeeeeeeee eeeeeeee e eeeeee eeeeeeeee eeeeeeee eeee eeeeeeeee eeeeeeee eee eeeeeeee. (Meeee 8, eeeeeee 8888).

Meeeeeeeeeeeeee (88) eeeeee eeee M-eeeeeeeeeeeeeeeeeee eeeeeeeeeeeee (88) ee eeeeeeeee eeeeeee/eeeee eeeeeee eee ee eee eeeeeeee ee eeeeee eeeeeeeee ee eeee 8,8-eeeeeeee-8,8-eeeeeeee-8,8-eeeeeeeeeeeeeeee (88).[‌8‌]

Meeeee 8 Meeeeeeeeee ee 8,8-Meeeeeee-8,8-eeeeeeee-8,8-eeeeeeeeeeeeeeee[‌8‌]

Mee eeeeeeee eeeeeeee ee eeeeeeee ee eee eeeeeeeeeeeee ee eee eeeeee eeee eeeeeeee ee e eeeeee eeeee ee eeee eee eeeeeee eeeeeeeeeeee 88, eeeee eeeeeeeee 8,8-eeeeeee eeeeeeeeeeeee eeeeee eee eeeeee eeee ee e eeeeee eeeeee eeeeeeee (Meeeee 8). Mee eeeeeeeee eeeeeee eee ee eeeeeee eeeeeeeeeee eee eee eeeeeeee ee eee eeeeeeeee eeeeeee eeee M-eeeeeeeeeeeeeeeeeee (Meeeee 8). Meee, eeeeeee e eeeeeee ee 8-eeeeeee-8-eeeeeeeeeeee (88) eee M-eeeeeeeeeeeeeeeeeee eeeeeeeeeeeee (88) ee e eeeeeee/eeeeeee eeeeee eeeeeeeee eeeeeeeeee ee 888°M eee 88 eeeee eeeee eeeeeee 88 ee 88% eeeee. Meeeeeeee ee 88 eeee eeeeeeeeeeeeeeeee eeeeeeeeeeeee ee eeeeeee ee eeeeee eeeee eee eeeeeee eeeeeeeeeee 88 ee 88% eeeee.

Meeeee 8 Meeeeeeeeee ee Meeeeeee 8,8-Meeeeeee-8-(8-eeeeeeeeeee)-8,8-eeeeeeeeeeeeeeee-8,8-eeeeeeeeeeeee[‌8‌]

Meeeeeeee eeeeee eeeeeeeeee (88) eeeeee eeee M-eeeeeeeeeeeeeeeeeee eeeeeeeeeeeee ee eee eeee eeeeeeee eeeeeee ee 88°M eee 88 eeeee eeeeee eeeeee 8-[(eeeeeeeeeeeeeee)eeeeee]-8-eeeeee-8,8-eeeeeeeeeeeeeeee-8-eeeeeeeeeee (88) ee 88% eeeee (Meeeee 8).

Meeeee 8 Meeeeeeeeee ee Meeeee 8-[(Meeeeeeeeeeeeee)eeeeee]-8-eeeeee-8,8-eeeeeeeeeeeeeeee-8-eeeeeeeeeee[‌8‌]

Meeeeeeeeeee Meeeeeeee

Meeeee 8-[(Meeeeeeeeeeeeee)eeeeee]-8-eeeeee-8,8-eeeeeeeeeeeeeeee-8-eeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌8‌]

Me e eeeeee eeeeeeeeee MeMM (8.88e, 88eeee) ee M8M (8eM), eee eeeee M-eeeeeeeeeeeeeeeeeee eeeeeeeeeeeee (88; 8.8e, 8.8eeee) eeeeeeee ee eeeeee eeeeeeeeee (88; 8.88e, 88.8eeee) ee eeeeeee (88eM) (MMMMMMM: eeeeeeeeee). Mee eeeeeee eee eeeeeee ee 88°M eee 88e. Mee eee eeeeee eeee eeeeeeeee eee eee eeeeeee eeeee eee eeeeee eeee eeee eee. MeMe eeee eee eeeee (Me8MM8). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeee ee eeeeeeeeeeeeee (MeMMe/eeeeee 8:8) ee eeee eee eeeeeee; eeeee: 8.88e (88%).

References