Can anyone suggest a simple method for protecting one of the aldehyde groups of glyoxal and a method for deprotecting it after reaction to form a Schiff base?
as shown in Fig. 3 Left, beginning with a highly diastereoselective auxiliary-controlled Baylis–Hillman reaction between the Oppolzer sultam-derived acrylimide 9 (1 eq) and anhydrous 2,2-dimethoxyacetaldehyde (3.0 eq) using 1,4-diazabicyclo[2.2.2]octane (DABCO, 0.3 eq) as catalyst in dichloromethane at 23 °C (16 h). The product of the reaction had incorporated two molecules of 2,2-dimethoxyacetaldehyde, and had expelled the sultam auxiliary by internal lactonization, as anticipated based on precedent (27)
Direct Entry to Erythronolides via a Cyclic Bis[Allene]
Kai Liu; Hiyun Kim; Partha Ghosh; Novruz G. Akhmedov; Lawrence J. Williams
J. Am. Chem. Soc. 2011, 133, 14968–1497
Addition of the enolate derived from oxazolidinone 1 to commercially available dimethoxyacetaldehyde afforded the expected aldol product as a single isomer (2,90%).