Science of Synthesis

Chemler, S. R.; Wdowik, T., Science of Synthesis: Catalytic Oxidation in Organic Synthesis, (2017) 1, 382.

The aminooxygenation strategy has been used in the stereoselective synthesis of morpholines. The method, involving a stoichiometric amount of copper(II) 2-ethylhexanoate that, in the presence of base and a nucleophile (nitrogen source), transforms alkenes ‌81‌ with a tethered alcohol group into the corresponding oxygen heterocycles ‌82‌ (‌Table 10‌).[‌77‌] The reaction occurs with high stereoselectivity and is compatible with different nucleophiles (sulfonamides, amides, and azides). Formation of five-membered rings is also possible by this protocol.

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Meeeeeee Meeeeeeee		Meeeeee	eee	Meeeee (%)	Mee
Meeeee	Meeeeeeeeee
	MeMM8		–	88	[‌88‌]
	MeMM8		>88:8	88	[‌88‌]
	MeMM8		>88:8	88	[‌88‌]
	8-M8MM8M8MM8MM8		>88:8	88	[‌88‌]
	MMM(MM8)8MM8MM8		>88:8	88	[‌88‌]
	MeM8		88:8	88e	[‌88‌]
	MeMM8		88:8	88e	[‌88‌]
	MeMM8		>88:8	88	[‌88‌]

e Meeeeeeeee ee 8M MMM eeeeeeeeeeee.

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‌Meeeee 88‌ Meeeee-Meeeeeeee Meeeeeeeeeee ee Meeeeeeeeee Meeeeee Me Meee Meeeeeeeeeeeeeeee[‌88‌]

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Me 8888, e eeeeee-eeeeeeeee eeeeeeeeeeeeeeee eeeeee eeeeeeeeeeee eee eeeeeeeeeeee eee eeeeeeeeeee eeeeeeeeee eeeee (e.e., ‌88‌) (‌Meeeee 88‌).[‌88‌] Mee eeeeeeeeeee ee e eeeeee(M) eeee eee eeeeee eee(8,8-eeeeeeeeeeeeee) eeeeee ‌88‌ ee eee eeeeeeee ee eeeeeeeeeeeeeeeeeeee eee (eeeeeeeeeeeee)eeeeeee ee ee eeeeeee eeeeeeeee γ- eee δ-eeeeeeee ‌88‌ eeee e eeeeeeeeee eeeeeeeeeee eeeeee eeee eeee eeeeee ee eeeeeeeeeeeeeeeeee.

‌Meeeee 88‌ Meeeeeeeeeeeeeee Meeeee Meeeeeeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

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e Meeeeee eeeeee ee eeeeeeee eeeeeee eeee eee eeee.

e 8 eee% ee Me(MMMe)8MM8 eee 8 eee% ee eeeeee eee eeee.

Meeeeeeeeeee Meeeeeeee

γ-Meeeeeee ‌88‌ (e = 8); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meee eeeeeeee eeeeee ee eeeeeee eee eeeeee e eeeee eeeeee eee eeee ee e eeeee eeeee. Me eeeeee ee eeeee eeee eeeee ee eeeeeeee eeeeeeee eeeeee eeee eeeee, eeeeee eee eeeeeeeeeee eeeeeeeee eeeeeeeee eee eeeeeeee eeeeee eeeeeeee eeeeee ee eeeee.

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References