Science of Synthesis

Evano, G., Science of Synthesis, (2007) 20, 228.

Supplementary procedures rely on the use of organoboranes obtained by hydroboration of alkenes for C—C bond formation, which is a well-documented process. Most of these reactions involve the formation of tetracoordinated organoborates ‌56‌ between the electron-deficient boron and a nucleophilic carbon atom. The complex formation is followed by the 1,2-intramolecular migration of an alkyl group from the boron atom to the adjacent carbon atom to give ‌57‌; these anionic rearrangements usually occur with substitution of a leaving group (‌Scheme 20‌).[‌130‌,‌131‌] With a proper choice of both the nucleophile and the organoborane involved in the process, this method can be useful for the synthesis of carboxylic acids from alkenes with one- or two-carbon homologation and even in an asymmetric way.

‌Meeeee 88‌ M—M Meee Meeeeeeee eeee Meeeeeeeeeeee[‌888‌,‌888‌]

Mee eeeee eeeeeee eeeeeeeee eee eeee eeeeeeeeeeeeee eeeeeeee eee eeeeeeee ee 8-eeeee-8,8,8-eeeeeeeeeeeeeee ‌88‌, eeeeeeee ee e eee-eeee eeeeeeee eeee eeeeeee (eeeeeeeeeeeee eeee eeeee eeeeeeeee eeeeeeee ee eeeeeeee eeee eee eeeeeee eeeeeee ee eeeeee-8,8-eeeeeee), eeee (eeeeeeeeeeeeeee)eeeeeee ee eeeeeeeeeeeeeee ee eeee eee eeeeeeeeeeeee eeeeeeeeeee eeee ‌88‌ eeeee eeeeeeeee eeee eeeeeeee eeeeeeee eeeeeeee (‌Meeeee 88‌).[‌888‌] Meee eeeeee eee eeeeeeeee eeeeeeee eee eee eeeeeeee ee eeeeee eeeeeeeee ee eeeee eeeeee ee eee eeeeeeee eeeeee eee ee eeeeeeee eeeeeee eeeee.

‌Meeeee 88‌ Mee-Meeeee Meeeeeeeeee Meeee eeee Meeeeee eee Meeeeeee ee 8-Meeee-8,8,8-eeeeeeeeeeeeeee eeee (Meeeeeeeeeeeeee)eeeeeee[‌888‌]

Meee eee eeeeeee ee eeeeeeeeeeeee eeee, eeeee eeeeeee eeeeeeeee eee eeeeeee eeeee eee e eeeeeeee eeeeeee eeeee, ee eeee ee eee eeeeeeeeeee ee eeee eeeeeeee, e eee-eeeeee eeeeeeeeeee eeeeeeeeee eeee ‌88‌ ee eeeeeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Mee-Meeeee Meeeeeeeeee Meeee eeee Meeeeee eee Meeeeeee ee Meeeeeeeeeeee eeee eee Meeeeee ee Meeeeeeeeeeee Meee[‌888‌]

Me eee eeeee (eeeeeeeeeeeee eee eeeeeeeeeeee), eeee eeeeee ee eeeeeeeeee eeeee eee ee eeeeeeee eeeee eeee eeeeeeeee. Meeeeeeeeee, eee eeeeeeee eeeeeeeeee eee eeeeeeee ee eeeeeee eeeeeeeeee eeeeee eeeeeee ee eee eeeeeeee eeeeeee, eeee ee eeeeeeee, eeeeeee, eeeeee, ee eeeeeeeeee (‌Meeee 88‌). Meeeeeee, eeee eee eeee eeeeeeeee 8-eeeeeeeeeee[8.8.8]eeeeee ee eeee eee eee eeeeeeeeeeeee eeee, eee eeeeeeeee eeeeeee eeeeeeee ee eee eeeeeeee ee eeeeeee eee eeeeeeeee eee eee eeee-eeeeeeeeeee eeeeee eeee eeee eee eeeeeeee eeeeeeee ee e eeeeeeee.

‌Meeee 88‌ Mee-Meeeee Meeeeeeeeee Meeee eeee Meeeeee eee Meeeeeee ee Meeeeeeeeeeee eeee eee Meeeeee ee Meeeeeeeeeeee Meee[‌888‌]

Meeeee	Meeeeeeeee Meeee	Meeee (%)	Mee
		88	[‌888‌]
		88	[‌888‌]
		88	[‌888‌]
		88	[‌888‌]
		88	[‌888‌]
		88	[‌888‌]
		88	[‌888‌]

e Meeeeeee ee eeeeee eeeeee eee eeeeeeeeeeeeeeee

Meeeeeeeee eeeeeeeee eeeeeeeeeeeee ee e eeee-eeeeeeeeee eeeeeeee eeeee ee eeeee eeee eeeeeeeee eeee eeeeeee- eee eeeeeeeeeeeeeeee (eeeeeeee eeeeeeeeeee ee eeee eeeee eeeeeeee ee “eeeeeeeee” eeeeeeeeeeeee). Meeeeee eeeeeeeee eeeeeeeee eeeeeeeeee eeeeeeeeeeeee eeeeeee eeee eeee eeeeeeee, eeeee eee eeeeeeeeee ee ee eeeeeeeeeeee eeeee eeeeee ee eeeeeeeeee.[‌888‌] Meeee Meeeeee'e eeeeeeeeee eeeeeeeeeeeee eeeeeeee eeeeeeee ee eeeeeeeee eeee eeeeeee, eeeeeeeeee eeeeeeee eeeeee ‌88‌ eee eeeeeeee (‌Meeeee 88‌). Meee eeeeeee eeeeeeeeeeee ee ‌88‌ eeee (eeeeeeeeeeeeee)eeeeeee,[‌888‌] eeeeeeee ee ee eeeeeeeee eeee, Meeeeee eee ee-eeeeeee eeeeeeee ee eeeeeeeee eeeeeeeeee eeeeeeeeeeeeee ee eeeeeeeeeee ‌88‌ eeee eeeeeeeeee eeeee ‌88‌ ee eeee eeeeee eee eeeeeeeeeeee eeeeeeee.[‌888‌] Meee eee eeeeeee eeeeeeeee ee eee eeee eeeee, ee eeeeeeeeeee ee ee eeeeeeeeee eeeeeeeee ee eeeeeeee eeeee Meeeeeee [(M)-(–)-eeeeeeeeeeee{8-[(M)-8-(eeeeeeeeeeeeeeeee)eeeeeeeeee]eeeee}eeeeeeeee] ee eee eeeeee eeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeeee Meeeeeeeee Meeee eeee Meeeeee eee Meeeeeeeee Meeeeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeee Meeee ‌88‌; Meeeeee Meeeeeeee:[‌888‌]

Mee eeeeeeeeeeeeee eee eeeeeeee ee eeeeee e 8.88 M eeee ee MM8•MMM (8.88 eM, 8.888 eeee) ee e eeee ee eee eeeeee (8.8 eeee) ee MMM (8 eM) ee 8°M. Mee eee eeee eee eeeeeee, eee eee eeee eee eeeeeee eee 8 e ee ee. Mee eeeeeee ee eeeeeeeeeeeee eeee eee eeeeeeee ee eeeeee, ee 8°M, e eeee ee eeeeeeeeeeeee eeee (888 ee, 8.8 eeee) ee MMM (8 eM) ee ee MMM eeee [eeeeeeee ee 8°M eeee eMe8MM (8.88 eM) ee MMM (8 eM) eee e 8.88 M eeee ee MeMe ee eeeeeee (8.88 eM)] eee eeeeeeee eee eeeeeee eee 8 e ee 8°M. Mee eeeeeeeeeeeeee eee eeee eeeee eee eeeeeee ee e eeee ee eee eeeeeeeeeeeee eeee eeeeeee ee 8°M eee eee eeeeeee eee eeeeeee ee 88°M eeeee eeeeeeeeee. Mee eeeeeee eee eeee eeeeee ee 8°M eee 8 M MeMM eeee (8 eM) eee eeeee eeeeee, eeeeeeee ee eee eeeeeeee eeeeeeee ee 88% M8M8 (8 eM) ee 8°M. Mee eeeeeee eee eeeeeee eee 8 e ee 8°M eee Me8M (88 eM) eee eeeee. Me eee eeeeeeeee eeeeeee eeeee eee eeeee Me8M (88 eM) eee eee eeee eee eeeeeeeee ee eee eeee eeeeeeee ee 8 M MMe ee ee, eeee eeeeeeeee eeee MeMe, eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeeee eeeeeee; eeeee: 88–88%.

References

Meeeeee Meeeeeeeeee

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