Science of Synthesis

Sartori, G.; Maggi, R., Science of Synthesis, (2007) 20, 597.

Various (hetero)cyclic compounds easily accessible even in optically active form have been utilized in the synthesis of 3- and 4-functionalized carboxylic acids. These heterocyclic starting compounds include epoxides, lactones, lactams, cyclic anhydrides, and dioxolanes. The reaction can be performed by treatment with nucleophilic reagents or, more simply, by hydrolysis or by hydrogenolytic ring opening.

α-Meeeeee-β-eeeee eeeee eeee eeee eeeeeeeeeee ee eeeeeeeee eeeeee eeee ee eeeeeeeeeeee eeee eeeeeee ee eee eeeeeeeeeee eeeeeeee.[‌88‌] Meeeeeeeeeee, eee eeeee- eee eeeeeeeeeeeeee eeeeeeeeee ee 8,8-eeeeeeeeeeeee eeee (‌88‌) eeee eeeeee eeeee ee eeeee eee ee eee eeeeeeee ee eeeeeee eeeeee(MM) eeeeeee ee eeeeeeeee ee eeeeeeee eee eeeeeee ee 88°M eee 8.8 eeeee, eeeeeeeee eee 8-eeeee eeeeeeeeee ‌88‌ ee 88% eeeee (‌Meeeee 88‌). Meeeeeee ‌88‌ ee eeeeeee ee eeee eeee eeeeee eeeeeeeeeee eee eeeeeeeee eeee 8-eeeee-8-eeeeeeeeeeeeeee eeee ‌88‌ ee 88% eeeee eee 88% ee.[‌88‌]

‌Meeeee 88‌ Meeeeeeeeee ee 8-Meeee-8-eeeeeeeeeeeeeee Meee[‌88‌]

M eeeeeeeee eeeee eee eee eeeeeeeeee ee β-eeeeeeeeeeeeeeeee eeeee eeee eee eeeeeeeeeeeee β-eeeee eeeee ee 88–88% eeeee ee eeeee ee eee eeeeeeeeeeee ee β-eeeeeee.[‌88‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeeeeeeee β-Meeee Meeee[‌88‌]

8-Meeeeeeeeeeeeee eeeee ‌88‌ eee eeeeeee eeee M-eeeeeeeeeeeeeeeeeee eeeee M-(8-eeeeeeeeeeeeeeeeeee)-M′-eeeeeeeeeeeeeeeee (MMM) ee eeeeeeeeeeeeeee/eeeee eeeeeeee ee eM 8.8 ee eeee M-eeeeeeeeeeeeeeeeee ‌88‌, eeeee eeee eeeeeeeee eeee eeeeeeeeeeeeeeeeee eee eeeeeee eeeeeeeeeeeeeeee ee eee eeeeeeeeeeeeeee eeeee Meeeeeeee eeeeeeeeee eeeeeee β-eeeeeee ‌88‌ ee eeee eeeee. Meeeee eee eeeeeeeeeee eeeeeeee ee eeeeeeeee ee eee eeeeeeeeeeeee ee eee β-eeeeeeee eeeeee. Mee β-eeeeeee ‌88‌ eee eeee eeeeeeeee eeee eee eeeeeeeeeeeee β-eeeee eeee eeeeeeeeeee ‌88‌ eeeee eeeeee ee eeeee eeeeeeeeee eeeeeeeeee ee eeeeeeeee eeeee. Meeeeeeeeeeeee ee eeeeeeeee ‌88‌ eeee eeeeeeeee ee eeeeeeee ee eeeeeeee ee eeee eeeeeeeeeee ee eeeeeeeeeee eeeeeeee eeeeeee eee β-eeeee eeeee ‌88‌ ee eeee 88% eeeeeee eeeee (‌Meeeee 88‌). Mee eeeeeeeeeeeee ee eee eeeeeeee 8-eeeeeee eeeee ‌88‌ ee eeeeeeeee eeeeee eee eeeee; eeee, eeeee eee eeeeeeeee eeeeee 8-eeeeeee eeeee eee eeeeeee eeeeeeee eeeeeeeee ee eee Meeee eeeeee eeeeeeeee eeeeeeee, eee eeeeee eeeeeeeeee ee eeeeeeeee eeeee eee eee eeeeeeeeeee ee eeeeeeeee eeeeee, eeeeeeeee eeeeeeeeeee β-eeeee eeeee.

Mee eeeee- ee eeeee-eeeeeeee MM8 eeee-eeeeeee eeeeeeee ee β-eeeeeeee eeeeeeeeee ee eeeeeeeee eeeee ee eeeeeeeee eeee eeeeeee β-eeeeeeeeeeeee eeeeeeeeeeeeeee. Meeeeeee, eee eeeeeeee ee eeeeeeeeeeeeee ee eeeeeeeeeeeeeee β-eeeeeeee eee eeeeeeee ee eeeeeeee eeeeeeeee (‌Meeeee 88‌).

M eeeeee ee eeeeeeeeeeeeeeee eeeeeeee β-eeeeeeee [eeeeeeee ee eee eeeeeeeeee eeeeeeeeeeeeeeeee ee eeeeee eeeeeee eeee e eeeeeee ee eeeeeeeee eeeeeeeee eeeeeeeee ee e eeeeee eeeeeeee(MMM)–eeeeeeee eeeeeee][‌88‌] ee eeeeeeeee ee eeeeeeeee eeee eeeeeee eeee eeeeee eeeee ee eeeeeeee eeeeeeeee ee 88°M, eeeeeeeee ee eee eeeeeeeeee ee β-eeeee eeeee ee 88–88% eeeee eeee eeeeeeeee ee eeeeeeeeeeeee ee eee eeeeeeee β-eeeeeee eee ee eee MM8-eeee eeeeeeee eeeeeeeee (88–88% ee) (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeee ee e 8-Meeeeeeeeeeeeee Meee ee Meee Meeeeee ee e β-Meeeee[‌88‌]

Meeeeeeeee eeeee eeeeeee eeeeeeeeeee ee eee 8-eeeeeeee eee ee eeeeeeeee eeeeeeee ee eeee eeeeeee ee eeeeeee eeeeee eeeeeeeeee (88–88% eeeee). Mee eeeeeee, 8-eeeeeeeeeeeeeee eeeee eee ee eeeeeeeeeee eeeeeeee ee eeeeeeeee ee eeeeeeeeeeeeeeeeeee eeeeee, eeeeeee eeee 8,8-eee(eeeeeeeeeeeee)eeeeeee, eeee 88 eee% eeeeeeeee ee eeeeeeee eee eeeeeeee (888 eMe) ee eeeee eeeeeee (‌Meeeee 88‌).[‌88‌] Mee eeeeeeeeeee eee eeee eeeeeeeeeeee eeeeeee ee eee eeeeeeeeee ee 8-[8M]-8-eeeee-8-eeeeeeeeeeeee eeee ee 88% eeeee eee 88% eeeeeeee eeeeeeeeee.

‌Meeeee 88‌ Meeeeeeeeeeee ee Meeeee Meeeeeeeeeeeeeeeeee Meeeee[‌88‌]

Mee eeeeeeeee ee eeeeeee M-eeee eeeeee eeeeee ee eeeeeeeee eeee eee 8,8-eeeeeeeeeeeeeeee 8-eeeee–eeeeeeee(eeeeeeeeeeeeeeeeeeeeeeee)eeeeeeeee(MM) eeeeee [MeMe8(eee)] eeeeee ω-(eeeeeeeee)eeeeeeeeee eeeee ee eeeeee ee 88–88% (‌Meeeee 88‌).[‌88‌] Mee eeeeeeee ee eeeeeeeee ee eeeeeeeee eeeeeee eeeee ee eeeee eeeeeeeeee ee 88°M eee 88 eeeee.

‌Meeeee 88‌ Meeeeeeeeee ee M-Meeeeeeeeeeeeee Meee[‌88‌]

M eeeeeee eeeeeeeeeee eeeeee eee eeee eeeeeeeee ee eeeeeee eeeeeeeeeeeeee eeee 8-eeeeeeeeeeeeeee eeeee. Meee eeeeeeeeeeeeeeeeeeee ee eeeee ee eeeeeee eee[(M)-8-eeeeeeeeeee]­eeeee ee eee eeeeeeeeeeeeeee ee −888°M eeeeeeee ee 8-(8-eeeeeeeeeeee)eeeeeeeeeeeee eee eee eeeeeeee eeeeeee ee eeeeeee eee 88 eeeeeee eeeeeeee ee eeeeeeee ee eeeeeeeeeeeee eee eeeeeeeee eeeeee eeeeeeeee, (M)-8-(8-eeeeeeeeeeee)-8-(eeeeeeeeeeeeeee)eeeeeeeeeee ee eeeeeeee ee 88% eeeee. Meee eeeeeeee, eeeeeeeee ee eeeeeeeeeeeeeee/eeeeeeee, ee eeeeeeeeee ee eeee (M)-(–)-8-eeeee-8-(8-eeeeeeeeeeee)eeeeeeee eeee [(M)-(–)-eeeeeeee] ee 88% eeeee eee 88% ee ee eee eeeeeeeeeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeeee ee (M)-(–)-8-Meeee-8-(8-eeeeeeeeeeee)eeeeeeee Meee[‌88‌]

Mee Meeeeee eeeeeeee eee ee eeeeeeeeeee eeeeeee ee eee eeeeeeeee ee 8-eeeeeee-8,8-eeeeeeeeeeeeeeeeeee eeee ee 88–88% eeeee (‌Meeeee 88‌).[‌88‌] Meee, eeeeeeee eeeeeeeee eeeeee eeee 8 eeeeeeeeeee ee eeee(eeeeeeeeeeeeee) eeeeeeeee ee eeee eeeeeeeeeee eeeee e eeeeeeee eeeeeeeeee, eeeeee eee eeeeeee ee 88% eeeee.

‌Meeeee 88‌ Meeeeeeeeee ee 8-Meeeeee-8,8-eeeeeeeeeeeeeeeeeee Meee[‌88‌]

Meeeeeeeeeee Meeeeeeee

(8M,8M)-8-Meeee-8-eeeeeeeeeeeeeee Meee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeee eeeee eee eeeeeee ee eeeeeee eee ee eeeeee eeeee. Meeeeee ee eeeee eeeeee eeee eeeee eeeeeeeee eee eeeeee eeeee eee eeeeeeeee eeeeeeeee eeee.

8,8-Meeeeeeeeeeee eeee (‌88‌; 8.8 e, 88 eeee) eee eeeeeeeee ee M8M (88 eM). Meeeeeee MeM8 (8.888 e, 88 eeee) eee 8.8 M ee Me(MM8)8 (88 eM) eeee eeeee eeeee eeeeeeee (eeeeeeeee eM 8.8–8.8) eee eee eeeeeee eee eeeeee ee 88°M. Meeee 8.8 e (eM ~8.8), eee eeeeeee eee eeeeee ee 8°M eee MeMM8 (8.888 e, 88 eeee) eee eeeee eeeeeeeeeee. Meeee 88 eee ee 8°M, eee eeeeeee eee eeeeeeee, eee eee eeeeee eeeeee eee eeeeeeeee eeeeeeeeeeeeee. Mee eeeeeee eeeeee eeeeeee eeee eeeeeeeee ee eee (eeeeeeeee eeeee) eeee e eee eeeee ee eeeee MMe, eee eeeeeee ee ee eee-eeeeeeeeee eeeee (Meeee 88MM8–888). Meeeeee eeee 8.8 M MM8MM eeee e eeeee, eeeeeeeeeee eeeee; eeeee: 8.88 e (88%).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 88/8, 888.
• 8.Meeeee-Meee, (8888) 88/8, 888.
• 8.Meeeee-Meee, (8888) 88/8, 888.