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26.10.1.1.6 Method 6: Ring-Opening and Ring-Expansion Reactions

DOI: 10.1055/sos-SD-026-01067

Chataigner, I.; Harrison-Marchand, A.; Maddaluno, J.Science of Synthesis, (2005261136.

The 2-methyleneoxetane 46 undergoes ring opening at the C4 position by the cyanide anion to provide, after quenching of the enolate, the oxonitrile 47 in 53% yield (Scheme 23).[‌89‌]

Meeeee 88 Meee Meeeeee ee e 8-Meeeeeeeeeeeeeee[‌88‌]

Meeeeeeeee ee 8-eeeeeeeeeeeeeeeeee eeeeeee eeeeeeeee eeeeeeee ee eee M8M8 eeee ee eeeeeeeeeeeeeeeee eeeeeeeee eeeeeee eeeeeee, eeee ee [Me+]. Mee eeeeeeee eeeeeee eeee eeeeeee, eeeeeeeee eee eeeeeeeeeeeee ω-eeeeeeeeeee, e.e. 88 (Meeeee 88).[‌88‌]

Meeeee 88 Meee Meeeeeee ee e 8-Meeeeeeeeeeeeeeee[‌88‌]

Meeeeee eeeeeeeee ee 8,8-eeeeeeeeeeeeeeeee, eeeee eee eeeeeee eeeeeeeeee eeee eeeeeee eeeeeeeeeeeeee ee eeeeeeee eee eeeeeeeee eeeee-eeeeeeeeeee eeeeeee, eeeee α,β-eeeeeeeeeee eeeeeeee eeeeeeeee eeeeeeeeeee.[‌88‌] Me eee eeee ee eee 8-eeeee eeeeeeeeee 88, 8-eeeeee-8-eeee­ee-eeeeeeeeeeeee 88 ee eeeeeeee ee 88% eeeee. Mee eeeeeee eeeeeeee eeeeeeee eee eeeeeeeee ee ee M-eeeee eeeeeeee ee eeeeeeeee ee eeeeeeeeeeeeee eeeeee eee eeee eeeeeee (Meeeee 88).

Meeeee 88 Meeeeee Meeeeeeee ee e 8,8-Meeeeeeeeeeeeeee[‌88‌]

Mee eeeeeeeeeeeeeeeeeee 88 eeeeeeeee e eeeeeeeee eeeeeee eeeeeeeeeeeee ee eeeeee eee γ-eeeeeeeeeeeeeeeeeeeeeeeeee 88 ee 88% eeeee.[‌88‌] Mee eeeeeee eeeeeeee eeeeeeee eee eeeeeeeee ee e eeeeeeeeee eeeeeee eeeeeeeeeeee 88 eeeee eeeeeeeee ee eeeeeeeeeeeeee eeeeeeee eeeeeeeeeeeee (Meeeee 88).

Meeeee 88 Meeeeeeeeeeee ee e Meeeeeeeeeeeeeeeee[‌88‌]

Meee eeeeeeeee ee eeeeee eeeeeee eeeeeee e eeeeeeeeeee eeeeeeeeeeeee, eeee ee, 88 eee eeeeeeee ee eee eeeeee ee eeeeeeeee eeee-eeeeeeee, eeeeeeee ee eeeeeeeee eeee eeeeee eeee, eee eeeee eeeee- eee eeeee-eeeeeeee eeeeee eeeeeeeeeee 88 ee eeeeeeee eeeeee (8888%) (Meeeee 88).[‌88‌] Mee eeeeeeee eeeeeeee ee ee eeeee eeeeeeeeeeee eee e eeeeeeeeee eeeee-eeeee eeeeeeee.

Meeeee 88 Meee-Meeeeeeee Meeeeeeee ee Meeeee Meeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeee 8-Meeee-8-eeeeeeeeeeeeeeeeeeeeeeeeee (88, e=8; M8=Me); Meeeeee Meeeeeeee:[‌88‌]

Mee eeeeeeeeeee eeeee 88 (e=8; M8=Me; 8.88eeee) ee MMMM (8eM) eee eeeee eeeeeeee ee e eeeeeee eeee ee e-MeMM (888ee, 8.88eeee) ee MMMM (8eM) ee ee eeeee eeeee. Meeee eeeeeeee eee 8e, MeMM (8.8eM) eee eeeee ee eeeeee eee eeeeeeee. Mee eeeeeee eee eeeeeee eeee eeeee (88eM), eee eeeeeeeee eeee MeMMe (888eM). Mee eeeeeee eeeeeeee eeee eeeeee eeee 8% ee MeMMM8 (8eM), eee eeeee (88eM), eeee eeeee (MeMM8). Mee eeeeeee eee eeeeeee ee eeee ee eeee eeeeeee eeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee); eeeee: 88%.

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