129886-62-0

Upstream product

• 100-39-0 benzyl bromide 
• 131233-30-2 (2S)-2-(1,3-dithian-2-yl)-1-propanol 
• 109-80-8 1.3-propanedithiol 
• 129886-61-9 (2R,4S,5R)-2-((S)-2-Benzyloxy-1-methyl-ethyl)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidine 

Downstream Products

• 79027-28-4 (2S)-3-(benzyloxy)-2-methylpropanal 
• 79026-61-2 (R)-3-benzyloxy-2-methylpropanal 

Relevant academic research and scientific papers

NOREPHEDRINE DERIVED 2-METHOXY OXAZOLIDINES AS CHIRAL FORMYL CATION EQUIVALENTS

Lewis acid catalyzed reaction of silylenolethers with 1 followed by a straightforward nondestructive removal of the chiral auxiliary affords the corresponding aldehydes in good e.e.Compound 1 respresents the first effective synthetic equivalent of formyl cation.

Room-temperature metallation of 2-substituted 1,3-dithiane derivatives and subsequent coupling with 2,3-disubstituted oxiranes

2-Substituted 1,3-dithiane derivatives, (S)-1(t-butyldiphenylsiloxy)-2- (1,3-dithian-2-yl)propane (9), (S)-1-(t-butyldimethylsiloxy)-2-(1,3-dithian- 2-yl)propane, 1-(t-butyldiphenylsiloxy)-2-(1,3-dithian-2-yl)-2-methylpropane, and 1,2-bis-(t-butyldiphenylsiloxy)-3-(1,3-dithian-2-yl)propane, were subjected to lithiation in THF with n-BuLi at room temperature (r.t.); the resulting anions reacted with 2,3-disubstituted oxirane, trans-2-methyl-3- (triphenylmethoxymethyl)oxirane(22), at r.t., giving the coupling products in satisfactory yield. On the other hand, the lithium salt formed in ether from (S)2-(1,3-dithian-2-yl)-1-(4-methoxybenzyloxy)propane with n-BuLi at r.t. reacted with 22 at r.t. in the presence of hexamethylphosphoric triamide to afford the coupling product in moderate yield. In addition, a mixed organometallic reagent, n-BuLi/Bu2Mg, was found to be an effective metallation reagent for 9 and the resulting anion reacted with 22 to afford the coupling product in good yield.