Science of Synthesis

Breit, B., Science of Synthesis, (2007) 25, 283.

A moderate preference for the linear aldehyde is usually observed for simple monoalkyl-substituted terminal alkenes when standard catalysts such as rhodium–triphenylphosphine are employed. This regiochemical preference for the linear isomer may be enhanced if the alkene substituent is a secondary or tertiary alkyl group. In these cases, complete regioselectivity in favor of the linear isomer can be obtained frequently. A typical example is given with the hydroformylation of homoallylic alcohol ‌15‌ (‌Scheme 4‌). After hydroformylation and oxidation of the lactol ‌16‌, the corresponding lactone ‌17‌ is obtained in good yield as a single regioisomer.[‌41‌,‌42‌]

‌Meeeee 8‌ Meeeeeeeeeeeee Meeeeeeeeeeeeeee ee M8-Meeeeeee Meeee-Meeeeeeeeee Meeeeeee Meeeeee[‌88‌,‌88‌]

Me eeeeeeee ee eeeee-eeeeeeeeeee eeeeeeee eeeeeee, eeee-eeeeeeeeeeeeeee eeeeeee eeeeeeeeeeeeee eeee eee eeeeeeee eeeeeeeeeee (‌Meeeee 8‌). Me eee eeee eeeeeeee eeee eee eeeeeeeee eeeeeeee ee eee ee eee eeeeeeeee ee e π-eeeeee–eeeeeee eeeeeeeeeeee.[‌88‌,‌88‌]

‌Meeeee 8‌ Meeeeeee-Meeeeeeee Meeeeeeeeeeeeeee ee Meeeeeee Meeeeeeeeee[‌88‌–‌88‌]

‌Meeeeeeeeee 8‌

Me8	Meeeeeeeee	Meeeee	Meeeee (Meeeee/Me/M)	Meeee (Meeeeeee/ Meeeee)	Meeeeeeeee (%)	Mee
Me	Me(eeee)(MM)8, M8/MM (8.8 MMe), 88°M, 88 e	–	888:8:8	88:8	88	[‌88‌]
Me	[Me(eee)]+MMe8−, M8/MM (8.8 MMe), 88°M, 88 e	–	88:8:8	88:8	88	[‌88‌]
Me	Me(eeee)(MM)8, M8/MM (8.8 MMe), 88°M, 88 e		888:8:8	88:8	>88	[‌88‌]
Me	Me(eeee)(MM)8, M8/MM (8.8 MMe), 88°M, 88 e	Me8M	888:8:8	88:8	88	[‌88‌]
8-eeeeeee-8-eeeeeeee	Me(η8-M8M8)8, M8/MM (8.8 MMe), 88°M, 88 e		88.8:8:8	88:8	>88	[‌88‌]
8-M8MM8M8	MeM(MMe8)8, 88°Me	–	e.e.	88:8	88	[‌88‌]
8-MeM8M8	MeM(MMe8)8, 88°Me	–	e.e.	88:8	>88	[‌88‌]
	MeM(MM)(MMe8)8, M8/MM (8.8 MMe), 88°M, 88 e	Me8M	888:8:88	88:8	88	[‌88‌]
8-eeeeeee	MeM(MM)(MMe8)8, M8/MM (8.8 MMe), 88°M, 88 e	–	e.e.	88:8	>88	[‌88‌]

e Meeee eeeeeee eee eeeeeeee.

e e.e. = eee eeeeeeee.

Meeeeeee, eeeeeee eeeeeeeeee ee eeeeeeee-eeeeeeeeeee eeeeeeeeeee, eeee ee eeeee eeeeeee, eeeeeeeeeeeeeeee, eeeeeee eeeeee, eeeee eeeeeeee, ee eeeee eeeeeeeeee, ee eeee ee eeeeeeee-eeeeeeeeeee eeeeeeeeeee, eeee ee eeeeeee e eeeeee eeeeeeeeee eee eee eeeeeeeee ee eee eeeeeeee eeeeee (‌Meeeee 8‌).[‌88‌–‌88‌] Me eee eeee eeeeeeeee eeee eeee eee ee eee ee eee eeeeee eeeeeeeee ee eee M—Mα eeee eeeeee eeee eeeeee eeeeeeeee eeeeeeee ee eee eeeeeeeeeee M—Mβ eeee eeeeeee ee eeeeeeeeeee eeeeeeeeeeeee ee eee eeeeee eeeeeeee eeeeee eeeeeeeeee ee eee α-eeeeee.[‌88‌]

‌Meeeee 8‌ Meeeeeee-Meeeeeeee Meeeeeeeeeeeeeee ee M8-Meeeeeeeeeeeee Meeeeeee Meeeeee[‌88‌–‌88‌]

‌Meeeeeeeeee 8‌

e Meee eee eeeeeeee.

e Meeee eee eeeeeeee.

Me eeeee eee eeeeee eeeeeeee eeeeeeeeeeeeee eeeeeeeeeeeeeeee ee eeeeeeee eeeee-eeeeeeeeeee eeeeeee, eee eeeeeeeeeeee ee e eeeee eeeeeee eeeeeeeeeee ee eee eeeeee eeeeeeee eee eeeeee eeeeee (‌Meeeee 8‌).[‌88‌,‌88‌] Meeeeeeee ee eeeeee eeeeeeeee eeeeeee eee eeeee eeeeeee eeeee eee eee eeeeeee eeeeeeee ee eee eeeeeeee eeeeeeeeeeee eeeeeee, eeeeeee ee eeeeeeeeeeee eeeeeeeee ee eeeeeeee ‌88‌ eeee eee eeeeee ‌88‌.

‌Meeeee 8‌ Meeeee Meeeeeee-Meeeeeeee Meeeeeeeeeeeeeee ee Meeeeeee Meeeeee eeee eee Mee ee e Meeeeee Meeeeee Meeeeeeeeee[‌88‌,‌88‌]

‌Meeeeeeeeee 8‌

Me eeeeeeee ee eeeeeee eeeeeeeee-eeeeeeee eeeeeeeeeeeeeeee, eee eee eeee ee eeeeee eeeeeeeee eeeeeeeee.[‌88‌] Meeee, eeeeeeeeeeee ee e eeeeeeee eeeeeeeeee eeeee ee e eeeee eeeeeeeee eeee eeeeee eee eeeeeeeeeeee ee eee eeeeeeee eee eeeeee ee e eeeeee eeeeeeeeeeeeee eeeeeeeeeeeeeeee eeeeeeeeee ee eeeeeeeee. Me eeeeeee ee eee eeeeeeeee-eeeeeeee eeeeeeeeeeeeeeee ee 8-(eeeeeeeeeeeeeeeee)eee-8-eee (‌88‌) (‌Meeeee 8‌).[‌88‌,‌88‌] Meeeeeee eeeeeeeeeeeeeeee ee eeeee ee eee eeeeeeee eeeeeee eeeeee ‌88‌ ee eeeeeeee, eeeee ee eeeeee ee ee eeee eeeeeeeee ee eee eeeeeeee eeeeeeee eeeeeee. Mee eeeeeeeeeeeeee eee eeeeee ee eeeeeeeeeeee ee eeeeeeee e eeeeeeeee eeeeeeeeeeee ‌88‌. Meeeeeeeee, eeeeeeeeeeeeeeee ee eee-8-eee (‌88‌) eeeee eee eeee eeeeeeeeee eeeee e eeeeeee ee eeeeeeee (‌88‌) eee 8-eeeeeeeeeeeee (‌88‌) ee e eeeee ee 88:88.[‌88‌,‌88‌] Meee e eeeeeeeee ee eeee ee eee eeeeeeeee eeeee, ee ee ‌88‌, eee eeeeeeee eeeeeeee ‌88‌ ee eeeeeeee ee eeeeeeeee eeeee.[‌88‌,‌88‌]

‌Meeeee 8‌ Meeeeeeeeeee Meeeeee Meeeee Meeeeeeee Meeeeeeee[‌88‌–‌88‌]

8,8-Meeeeeeeeeeee ee eeee ee eeeeeeeeeeeeee eeeeeee eeeeeeee eeeeee eeeeeeeee ee eee eeeeee eeeeeee (Meeeeeeee' eeee).[‌88‌] Meee ee eeeee eee eeeeeeee- ee eeee ee eeeee-eeeee eeeeeeeeeeeeeeee. Meee, eeeeeee eeeeeeeee ‌88‌, eeeeeeeeeee ee e eeeeeeeeeee eeeeeee eeee e eeeeee eeeeee, ee eeeeeeeeeeeeeee ee eeee eee eeeeee eeeeeeee ‌88‌ ee 88% eeeeeeeeeee (‌Meeeee 8‌).[‌88‌] M eeeee ee eeeeee ‌88‌ eee eeeeeeee ee eee eeee eeeeeee, eeeeeeeee eeee eeeeee eeeeeeeeeeeee.

‌Meeeee 8‌ Meeeeeeeeeeeee Meeeeeeeeeeeeeee ee e 8,8-Meeeeeeeeeeee Meeeee ee e Meeee Meeeeee[‌88‌]

M eeeeeee eeee eeeeeeeeeeeeeeee ee eeeeee eeeeeeeeeee eeeeeee ee eeeee eee eeeeeeeeee, eeeee eeeeeeee eeeee eeeeeeee eeeeeeeeee (eeeeeeee, eeeeeeeeeee). Mee eeee eeeeee, e eee ee eeeeeeeeeee eeeeeee ‌88‌–‌88‌ eee eeee eeeeeeeee, eeeeee eeee ee eeeeeee eeeeeeeee eeee eeeeeee eeeeeeeeeeeee eeeeeeee (‌Meeeee 88‌).[‌88‌,‌88‌] Meee eeeeee eee eee eeeeeeeeeeeeeeee ee 8,8- eee 8,8-eeeeeeeeeeeee eeeeeee ‌88‌–‌88‌ eeeee eeeeee eeee eeeeeeeeee (‌Meeeee 88‌).[‌88‌–‌88‌]

‌Meeeee 88‌ Meeeeee eeee Meeeeee Meeeee Meeeee Meeeeee Meeeeeeee eee eee Meeeeeeee Meeeeeeeeeeeeeee ee Meeeee Meeeeeeeeee Meeeeee[‌88‌–‌88‌]

‌Meeeee 88‌ Meeeeeeeeeeeeeee ee 8,8-Meeeeeeeeeeee Meeeeee eee Meeeeeeeeeee[‌88‌–‌88‌]

‌Meeeeeeeeee 88‌

e MMM = eeeeeeee eeeeeeeee = eee(eeeeeeeee) × eee−8(eeeeeeee) × e−8.

‌Meeeeeeeeee 88M‌

e MMM = eeeeeeee eeeeeeeee = eee(eeeeeeeee) × eee−8(eeeeeeee) × e−8.

‌Meeeeeeeeee 88M‌

e MMM = eeeeeeee eeeeeeeee = eee(eeeeeeeee) × eee−8(eeeeeeee) × e−8.

‌Meeeeeeeeee 88M‌

e MMM = eeeeeeee eeeeeeeee = eee(eeeeeeeee) × eee−8(eeeeeeee) × e−8.

‌Meeeeeeeeee 88M‌

e MMM = eeeeeeee eeeeeeeee = eee(eeeeeeeee) × eee−8(eeeeeeee) × e−8.

M eeeeeeee eee eeeeeee eeeeeeeee eeeeeee eeee eeeeeeeee ‌88‌ eee eeeeeeeeeee ‌88‌ ee eeeee eeee eeeeeeee eeeeee eeeeee eeeeeeeeeeeee. Meeeeeeeee, eee eeeeeeeeeeeeeeee ‌88‌ eeeeeeeee e eeeeeee eeeeeeee eeee eeeeeeee eeeeeeeee eeee eeeeeeee eeee ee eeeeeeeeeeeeeee eee eeeeeeee eee eeeeee eeeeeeeeeeeee (‌Meeeee 88‌).[‌88‌] Meee eeeeeeee eeeeeeee ee eeeeeeeee ee eeeeeeee-eeeeeeeee eeeeeeeeeeeeeeee ee ee eeeeee eeeeeeeeeeee eeeeee ee eeeeeee.

‌Meeeee 88‌ Meeeeeee-Meeeeeeee Meeeeeeeeeeeeeee ee Meeeeeeeeeeeeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

e Meeeeeee eeeeeeeeee: Me(eeee)(MM)8+eeeeee ee 88°M, MM/M8 (8:8, 8.8 MMe), eeeeeee (e8 = 8.888 M) eeeee 8 e (eeeeeeeee/eeeeee/eeeeeee = 8888:88:8).

References

Meeeeee Meeeeeeeeee

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