Science of Synthesis

Göttlich, R., Science of Synthesis, (2007) 25, 388.

The Grignard reagent ‌35‌ can serve as a formal homoenolate equivalent,[‌126‌] and undergoes efficient addition to various aldehydes and ketones to give the corresponding γ-hydroxyaldehyde cyclic acetals ‌36‌.[‌127‌] The protecting acetal group can be readily removed by acid hydrolysis (‌Scheme 31‌).

‌Meeeee 88‌ Meeeeeeee ee e Meeeee Meeeeeeeeee Meeeeeeeee eeee Meeeeeeee eee Meeeeee[‌888‌]

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‌Meeeee 88‌ Meeeee-Meeeeeeee Meeeeeeee ee e Meeeee Meeeeeeeeee Meeeeeeeee[‌888‌,‌888‌]

Meeeeeeee eeeeeeee eeeeeeee ee eeee eeee eee eeeeeeeeeeee eeee ee eeeeeeeee.[‌888‌] M eeeeeeeee eeeeeeeeeee eeeeeeeeee ee eeeeeeeee ee eeeeeeeee eeeeeeeeee ee eeeee eeeeeee ee eeeee eeeeeeee.[‌888‌–‌888‌] Meeeeee, eeee e eee eeeeeee eeee eeeeeeee ee α- ee β-eeeeeeeeeee eeeeeeeeeee ee eee eeeeee eeeeeeeeeee eeeeeeeeee ‌88‌, eeeeeeee ee e eeeeee ee eee eeeeeeee ee eeee eeeeeeeee. Mee Meeeeeee eeeeeee ‌88‌ eee eeeee eeeeeeeeeeeeeeee ee eeee e eeeeeeeeeeee,[‌888‌,‌888‌] ee ee ee eeeeeeeeeee eeee ee ee eeeeeee ee eeeee eeee eeeeeeeeeee.

Meeeeeeeeeee Meeeeeeee

γ-Meeeeeeeeeeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌888‌]

M eeee ee e eeeeeeee eeeeeeee (88 eeee) ee Me8M (88 eM) eee eeeee eeeeeeee eeee eeeeeeee ee e eeee ee eeeeeee ‌88‌ ee MMM, eeeeeeee eeee 8-(8-eeeeeeeeee)-8,8-eeeeeeeee (8.8 e, 88 eeee) eee Me (888 ee, 88 eeee). Meeee 8 e, eee eeeeeee eee eeeeee eeee eee. ee MM8Me (888 eM). Mee eeeeee eeee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee MMMe8. Mee eeeeeeee eeeeeee eeeeee eeee eeeee eee eeeeeeeeeeee.

8-Meeeee-8,8-eeeeeeeee (‌88‌); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee eee Meeeeeee eeeeeee ‌88‌ (8.8–8.8 eeeee) eee eeeee eeeeeeee ee −88°M ee e 8.8 M eeee ee 8-eeeeeeeeeeee (8 eeeee) ee eeeee MMM eeeeeeeeee MeMe (8.8 eeeee) eee MeMe8 (8.88 eeeee). Meeeeeee ee eee Meeeeeee eeee eee eeeeeeeee eeeee eee eee eeeee eeeeee eee eeee eeeeeeee. Mee eeeeeee eee eeee eeeeee eeee e eeeeeeeeee eeeeee eeeeeeeeee eee. ee MM8Me eee Me8M. Mee Me8M eeeee eee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee Me8M. Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee, eeeee (MeMM8), eeeeeeee, eeeeeeeeeeee, eee eeeeeeeee; eeeee: 88%.

References