Science of Synthesis

Phillips, A. J.; Love, C. E., Science of Synthesis, (2007) 20, 840.

The rearrangement of ketene acetals derived from treatment of allylic alcohols with ortho esters (‌Scheme 20‌) is a useful alternative method to the Ireland–Claisen rearrangement and is widely known as the Johnson ortho ester–Claisen rearrangement.[‌84‌]

‌Meeeee 88‌ Meeeeee Meeee Meeee Meeeeeeeeeeee[‌88‌]

Mee eeeeeeee eeeeeeeee eeeeeeee ee eeeeeeeee ee ee eeeeeee eeeeeee eeee ee eeeee eeeee ee eee eeeeeeee ee ee eeee eeeeeeee (eeeeeeeeee eeeeeeeee eeee, eeeeeeee eeeee eeeeeeeee eeee ee 8,8-eeeeeeeeeeeeeeeee eeee eee 8,8-eeeeeeeeeeeee eee eeee eeeeeeee) eeeee eeeeeee. Meee eee eeeee ee eeee ee eeeeeeeee, eeeee eeeee eeeeeeee ee eeeeeeee ee eee eeee ee e eeeeee ee eeee e eeeeee eeeeee, eeeee eeeeeeeee eeeeeeeeeeeee. Meeeeeee eee eeeeeeeeeeeee ee eeeeee eeeeeeeeeeeeeee, eee eeee ee e eeeeee eeee eeeeeeeeeee eeeeeee ee eeeeeeeee eeeeeeeeeeee eee eeeeeeee ee eeeeeeeeeee eeeeee eeeeeee eee eeeeee. Meeeeee ee eeee, eee eeeeeeee ee ee eeeeeeee eeeeeee ee eeeeeee eeeee eeeee ee ee α-eeeeeeeeeee, eeee ee eeee eeeee eeeeee ee eeeeee eeee, ee eeee eee eeeeeeeeeeeeeee ee eee α-eeeeeeee ee ee ee eeeeeeeeeee. Meeeeee eeeeeeee ee eeeeeee eeeeeee eeee eee eeeeeee eeeeeeeeee eee eeeee ee ‌Meeeee 88‌ (e.e., ‌88‌ eeee ‌88‌) eee ‌Meeee 8‌, eee eeeeee eeeeeeee eee eeeeeeeee ee ‌Meeeee 88‌ (e.e., ‌88‌ eeee ‌88‌) eee ‌Meeee 8‌.

‌Meeeee 88‌ Meeeeee Meeee Meeee Meeeeeeeeeeee ee Meeeeee Meeeeee[‌88‌]

‌Meeee 8‌ Meeeeee Meeee Meeee Meeeeeeeeeeee ee Meeeeee Meeeeee[‌88‌–‌88‌]

Meeeeeee	Meeeeeeeee	Meeeeee	Meeee (%)	Mee
	MeM(MMe)8, MeMM8M, 888°M		88e	[‌88‌]
	MeM(MMe)8, 8,8-eeeeeeeeeeeee (eee.), 888°M		88	[‌88‌]
	MeM(MMe)8, MeMM8M, 888°M		88	[‌88‌]
	MeM(MMe)8, MeMM8M, 888°M		88	[‌88‌]
	MeM(MMe)8, 8% e-MeMM8M, ­eeeeee, 88 e		88	[‌88‌]
	MeM(MMe)8, 8% e-MeMM8M, ­eeeeee, 88 e		88	[‌88‌]

e (8M/8M) 8.8:8.

‌Meeeee 88‌ Meeeeee Meeee Meeee Meeeeeeeeeeee ee Meeeee Meeeeee[‌88‌]

‌Meeee 8‌ Meeeeee Meeee Meeee Meeeeeeeeeeee ee Meeeee Meeeeee[‌88‌–‌88‌]

Meeeeeee	Meeeeeeeee	Meeeeee	Meeee (%)	Mee
	MeM(MMe)8, MeMM8M, 888°M, 88 e		88	[‌88‌]
	MeM(MMe)8, MeMM8M, 888°M, 8 e		88e	[‌88‌]
	MeM(MMe)8, MeMM (8.8 eeeee), eeeeee, 888°M, 8 e		88	[‌88‌]
	MeM(MMe)8, e-MeMM8M, eeeeee, eeeeee, 8 e		>88	[‌88‌]
	MeM(MMe)8, eeeeeee, MeMM8M, 888°M, 8 e, eeee MeMMe, MeMM		–e	[‌88‌]

e ee 8:8.

e Meeee eee eeeeeeee.

M eeeeee ee eeeeeeeeeeee ee eeeeeee eeeeeee eeee eeee eeeeeeeee. Mee eeeeeee, Meeee eeeeeeeee eeeeeee eee eeeeeeeeeeeee ee eeee ee eee eeeeeeeee ee eeeeeeeeeeeee M8 (‌Meeeee 88‌).[‌88‌] Meee eeeeeeee eeee eeeeeeeeeeee eeee eee eeeeeee eeeeeeeeeeee ee ee eeeeeeee ee eee eeee e eeeeee eeeeee ee eee eeeee eeeee (8 eeeeeeeeeee ee eeee eeeeeee).

‌Meeeee 88‌ Meeeeeeee ee Meeeeeeeeeeee M8 eee Meeeeee Meeee Meeee Meeeeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeee (8M)-8-[(8M)-8,8-Meeeeeee-8,8-eeeeeeee-8-ee]eeee-8-eeeeee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee eeee ee eeeeeee ‌88‌ (8.8 e, 88.8 eeee) ee MeM(MMe)8 (88 eM, 888 eeee) ee eee eeeeeeee ee MeMM8M (8.88 e, 8.8 eeee) eee eeeeee ee 888°M eee 8.8 e. Meeee eeeeeee ee ee eee eeeeeee ee eee eeeeeee ee eeeeeeeeeeee, eeeeeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eeeeeeee eee eeeeeee; eeeee: 8.88 e (88%).

Meeee 8-{(8M,8M,8M)-8,8-Mee[(8-eeeeeeeeeeeee)eee]eeeeeeee-8-ee-8-ee}eeeeeeeeee (‌88‌):[‌88‌]

M eeee ee ‌88‌ (888 ee, 8.888 eeee), MeM(MMe)8 (8.88 eM, 8.88 eeee), eee MeMM (88 ee, 8.88 eeee) ee eeeeee (8 eM) eee eeeeeee ee 888°M eee 8 e eee eeeeeee eeee MeMMe. Mee eeeeeeeee eeee eee eeeeee eeee 8 M MeMM eeee, eeeee (MeMM8), eee eeeeeeeeeeee. Mee eeeeeeee eee eee eeeeeeee ee eeeeeeeeeeeeee ee eeeeeee eee eeeee eeeee ‌88‌; eeeee: 888 ee (88%).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88e, 8888.
• 8.Meeeee-Meee, (8888) M 88e, 888.
• 8.Meeeee-Meee, (8888) M 88e8, 888.