Science of Synthesis

Podlech, J., Science of Synthesis, (2007) 25, 44.

It is often advantageous to oxidize silyl ethers ‌29‌ directly to give aldehydes ‌30‌, thereby avoiding a two-step deprotection/oxidation sequence. Reviews on the reactivity of compounds containing primary silyl ether groups and/or secondary silyl ether groups, and sometimes also unprotected hydroxy groups, toward numerous oxidizing agents have been published.[‌56‌,‌141‌,‌142‌] Typical oxidations of this type are collected in ‌Scheme 21‌.[‌3‌,‌51‌,‌143‌–‌147‌]

‌Meeeee 88‌ Meeeeeeee Meeeeeeee ee Meeee Meeeee Meeeeee eeee Meeeeee Meeeeeee[‌8‌,‌88‌,‌888‌–‌888‌]

‌Meeeeeeeeee 88‌

M8	MeM88	Meeeeeeeee	Meeee (%)	Mee
(MM8)8Me	MMM	MMMM, (MMMe)8, Me8M, −88 ee −88°M	88–88	[‌888‌,‌888‌]
(MM8)8Me	MMM	MMMM, (MMMe)8, Me8M, −88°M	88	[‌888‌]
	MMM	MMMM, (MMMe)8, Me8M, −88 ee −88°M	>88	[‌888‌]
Me	MeMeMe8	MeM8•ee8, ee, 8 eee	888	[‌8‌]
Me	MeMeMe8	MMM, ee, 8 eee	88	[‌8‌]
Me	MeMeMe8	MMM, MMM, ee, 8 eee	888	[‌8‌]
	MMM	MeM8•ee8, 88°M, 8 e	88–>88	[‌888‌]
	MMM	MeM8•ee8, eeeeee eee	88	[‌888‌]
	MMM	MMMM, (MMMe)8, Me8M, −88°M	88	[‌888‌,‌888‌]
	MMM	MMMM, (MMMe)8, Me8M, −88°M	88	[‌888‌]
	MMM	MMMM, (MMMe)8, Me8M, −88°M	88	[‌88‌]

Meeeeeeee, eeee-eeeeeeeeeeeeeeeeee eeeeee eee eeeeeeeeee eee eeeeeeeee ee eeeeeeeee, eee eeee eee ee eeee eee eee eeeeeeeeeeeeeee ee eeeeeee eeeeee.[‌888‌] Meeeeee' eeeeeee (MeM8•ee8)[‌88‌] eeeeee eee eeeeeeeee ee eeeeeee eeeeeeeeeeeeee eeeeee ee eee eeeeeeeeeeeee eeeeeeee eeeeeee eeeeeeeee eeeeeeeee eeeeeeeeeeeeee eeeeee.[‌888‌] Meeeee eee eeeeee eeee eeeeeeeeee eee eeeeeeee ee eee eeeeeeee ee eeeeee eee.[‌888‌] Meeeeeeee ee eeeeeee eeeeeeeeeeeeeeeeeee eeeeee eeee Meeeeee' eeeeeee eeee eeeee,[‌8‌] eee eeeeeeeeeeeeeeeee, ee eeee-eeeeeeeeeeeeeeeeee eeeeee eee eee eeeeeeee ee eee eeeeeeeeeeee.[‌888‌–‌888‌] Meeeeeeeee eeeeeeeeeeeeee eee eeee ee eeee eee eee eeeeeeeee ee eeeeeeeeeeeeee,[‌888‌] eeeeeeeeeeeee,[‌888‌] eee eeeeeeeeeeeeeeeeeee eeeeee,[‌8‌] eeeeeeee eee eeeeeeeeeee eee eee eeeeeeeee ee eeeeeee eeeeee eeeeeeeee eeeeeeee ee eeeee eeee eeee Meeeeee' eeeeeee. Meeeeeeeee eeeeeeeeee[‌88‌] eeeeeee eeee eeeeeeeeee eeeeeeeeeeeeee,[‌8‌] eee eeeeeeeeeeeeee-eeeeeeeee eeeeeee eeeeeeee eee eeeeeeee eeeeee eeee eeeeeeeee eeeeeeeee eeeeeeee, eeee eeeeee eee eeeeeeeeeee ee eeeee eeeee eeee eeee Meeeeee' eeeeeee.[‌888‌] Meeee eeeeeeeee eeeeee eee eeeeeeeee ee eeeeeeeeeeeeee eee eeeeeeeeeeeee eeeeee ee eeee eeeeeeeee, eee ee eee eeeeeeeee ee eee eeeeeeeee ee eeee-eeeeeeeeeeeeeeeeee eee eeee-eeeeeeeeeeeeeeeeee eeeeee (eee ‌Meeeee 88‌).[‌888‌] Meeee, eeeeeee eeeee eeeeee eee eeeeeeee eeeeee eeee eeeeeeeee eeee, e eeee eeee ee eeee eeeeeeeeeee ee eee eeeeeeeee eeeeeeeee ee eee eeeeeeeeeeeeee eeeee ‌88‌ ee eeeeee eee eeeeeeeeeeee eeee ‌88‌ (‌Meeeee 88‌).[‌888‌,‌888‌]

‌Meeeee 88‌ Meeeeeee Meeeeeeee ee 8,8,8,8,8-Meeeeeee-M-(eeeeeeeeeeeeee)-M-eeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeee [‌88‌, M8 = (MM8)8Me]; Meeeeee Meeeeeeee Meeee Meeee Meeeeeeeee:[‌888‌]

MMMM (8.8 eM, 88 eeee) eee eeeeeeeee (eeeeeeeee ee eee) eeeee ee −88°M ee e eeee ee eeeeee eeeeeeee (8.88 e, 8.8 eeee) ee eeeee MM8Me8 (88 eM). Meeee 8 eee, 8-(eeeeeeeeeeeeeee)eeeeee (8.88 e, 8 eeee) ee MM8Me8 (8 eM) eee eeeeeeeeee eeee eee eeee eeeeeee. Mee eeeeeeeeeee ee eee eeeeeee eee eeeeeee ee eeee ee −88°M eeee 88 eee, eee eeee ee eee eeeeeeeeee ee eeeeeee −88 eee −88°M eee e eeeeeee 88 eee. Meeee eeeeeeeee ee −88°M, Me8M (8.8 eM, 88 eeee) eee eeeee eee, eeeee e eee eee, eee eeeeeee eee eeeeeee ee eeee ee ee. Meeeeee eee eeeeeeee ee eee 8,8-eeeeeeeeeeeeeeeeeeeeee eeeeeeeeee, eeeeeeee eeeeeeee eeee eee eeeee eeeeeeee eeeeeee; eeeee: 8.88 e (88%).

Meeeeeeee ‌88‌; Meeeeee Meeeeeeee Meeee Meeeeee' Meeeeee:[‌888‌]

MMMMMMM: Meeeeeee(MM) eeeee eeee eeeeeeeee eee eeeeeeeeeee eeeeee eee ee eeeeeeeeee ee e eeeee eeeeeeeeee.

Meeeee eeeeee eee eeeeeeeeee eeeee MeM8 (8.88 e, 88 eeee) eee eeeeeeeee ee eeeee MM8Me8 (888 eM) eeeeeeeeee eeeee eeeeeeee (8.88 eM, 888 eeee) eee eee eeeeeee eee eeeeeee eee 88 eee. Mee eeee eeee eee eeeeeeee eee eeeeee ee 8°M eee e eeeeeee eeeeeeeeeeeeee eeeee (88 eeee) ee eeeee MM8Me8 (88 eM) eee eeeee. Meeee 8 e, eee eeeeeee eee eeeeeeee eeeeeee e eee ee eeeeee eee eee eee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeee eee eeeeeeee, eeeee eee eeeeeee eeeeeeeeeeee eeee eee eeeeeee eeeeeeeee.

References