126178-13-0

Upstream product

• 74181-34-3 2,2,-dimethyl-1,3-dioxan-5-one 
• 53104-32-8 (5-amino-2,2-dimethyl-1,3-dioxan-5-yl)methanol 
• 59983-39-0 (S)-1-amino-2-(methoxymethyl)pyrrolidine 
• 100-39-0 benzyl bromide 
• 126178-07-2 (S)-(+)-1-(2,2-dimethyl-1,3-dioxan-5-ylidenamino)-2-methoxymethylpyrrolidine 

Downstream Products

• 139153-20-1 ((4S,6S)-4,6-Dibenzyl-2,2-dimethyl-[1,3]dioxan-5-ylidene)-((S)-2-methoxymethyl-pyrrolidin-1-yl)-amine 
• 139153-24-5 (4S,6S)-4,6-Dibenzyl-2,2-dimethyl-[1,3]dioxan-5-one 
• 219746-02-8 (4S,6S)-4-Benzyl-6-benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-5-one 
• 421567-95-5 (4S,6S)-4,6-Dibenzyl-2,2-dimethyl-5-methylene-[1,3]dioxane 

Relevant academic research and scientific papers

Preparation and reactions of 2,2-dimethyl-1,3-dioxan-5-one-SAMP-hydrazone: A versatile chiral dihydroxyacetone equivalent

The SAMP-hydrazone of 2,2-dimethyl-1,3-dioxan-5-one represents a valuable chiral dihydroxyacetone equivalent. Asymmetric mono- or α,α′-bisalkylations followed by auxiliary cleavage leads to the corresponding mono- or α,α′-disubstituted, acetonide protected ketodiols in excellent diastereo- and enantiomeric excesses.

Asymmetric synthesis of pseudo C2-symmetric 2-methyl substituted 1,3-diols

The diastereo- and enantioselective synthesis of pseudo C2-symmetric, 2-methyl substituted, acetonide protected (4) and free 1,3-diols 5 employing the SAMP-hydrazone mothodology with virtually complete asymmetric induction (de ≥ 96%, ee ≥ 98-99

Diastereo- and enantioselective synthesis of α,α'-disubstituted, C2-symmetric ketones using the SAMP-/RAMP-hydrazone method

Starting from simple, symmetric ketones such as, 3-pentanone,1,3-diphenyl-2-propanone and 2,2-dimethyl-1,3-dioxan-5-one, α,α'-bisalkylation of the corresponding SAMP-hydrazones (S)-2 and (S)-8 [(S)-1 -(alkylideneamino)-2-(methoxymethyl)pyrrolidines and (S)-1-(2,2-dimethyl-1,3-dioxan-5-ylideneamino)-2-(methoxymethyl)pyrroli dines, respectively], followed by oxidative cleavage with ozone affords chiral, C2-symmetric ketones 5 and (S,S)-11 of high diastereo- and enantiomeric purity (de, ee > 98%).

Enantioselective Alkylation of 2,2-Dimethyl-1,3-dioxan-5-one Using the SAMP-/RAMP-Hydrazone Method

The lithiated SAMP-hydrazone (S)-3 is used as a chiral 1,3-dihydroxyacetone-enolate equivalent C in overall enantioselective α-alkylations leading to 4-alkyl-2,2-dimethyl-1,3-dioxan-5-ones (S)-5a-i in good overall chemical yields and of high enantiomeric purity (ee = 88 - >/= 93percent.