1279699-93-2

Upstream product

• 103-49-1 dibenzylamine 
• 503830-53-3 (R_S)-3-bromo-1-(p-tolylsulfinyl)butan-2-one 
• 1519-39-7 (R)-methyl p-tolyl sulfoxide 
• 1279699-92-1 (S)-3-(dibenzylamino)-1-[(R)-p-tolylsulfinyl]butan-2-one 

Downstream Products

• 127927-42-8 (2R)-[(1S)-1-(dibenzylamino)ethyl]oxirane 
• 1356546-06-9 (6S,7S)-7-(dibenzylamino)-6-hydroxyoctan-3-one 
• 1356546-23-0 C₃₂H₄₉NO₂ 
• 1383476-01-4 (2R,3S)-3-(dibenzylamino)-2-[(4-methoxybenzyl)oxy]butan-1-ol 
• 1383476-02-5 (2R,3S)-3-(benzylamino)-1-[(4-methoxybenzyl)oxy]butan-2-ol 
• 1383475-99-7 (2R,3S)-3-(dibenzylamino)-2-[(4-methoxybenzyl)oxy]butanoic acid 
• 1383476-00-3 (2S,3S)-1-benzyl-2-{[(4-methoxybenzyl)oxy]methyl}-3-methylaziridine 
• 1179529-31-7 (4S,5S)-3-benzyl-5-(hydroxymethyl)-4-methyloxazolidin-2-one 
• 910124-42-4 (2S,3S)-2-(dibenzylamino)hept-6-en-3-ol 

Relevant academic research and scientific papers

Stereoselective divergent synthesis of 1,2-aminoalcohol-containing heterocycles from a common chiral nonracemic building block

γ-N,N-Dibenzylamino-β-hydroxysulfoxide 1 proved to be an excellent chiral building block for the synthesis of a range of 1,2-amino alcohol-containing heterocycles. Thus, 1 was converted into 4,5-disubstuted oxazolidin-2-one 4 and aminoepoxides 2 and 3. Aminoepoxide 2 proved to be an excellent precursor to access oxazolidin-2-one 5 and azetidin-3-ol 6. Finally, 2 was used as a key intermediate that allowed the development of a divergent strategy to access cis-2-methyl-6-substituted piperidin-3-ol alkaloids. (+)-Deoxocassine 7 and a C-6 ethyl analogue 8 were prepared to illustrate this approach and to demonstrate that this strategy should be adaptable to the production of other members of this alkaloid family.

A divergent synthetic strategy based on the regioselective reductive ring-opening of a cyclic 1,2-p-methoxybenzylidene acetal

(1S)-N,N-Dibenzyl-1-[(4R)-2-(4-methoxyphenyl)-1,3-dioxolan-4-yl]ethanamine is obtained in five steps from an -bromo - (R)-sulfinyl ketone and is used as a common intermediate for the synthesis of the p-methoxybenzyl-protected primary and secondary alcohol

A route to "all-cis" 2-methyl-6-substituted piperidin-3-ol alkaloids from syn-(2R,1′S)-2-(1-dibenzylaminomethyl)epoxide: Rapid total synthesis of (+)-deoxocassine

A general strategy leading to the synthesis of two cis-2-methyl-6- substituted piperidin-3-ols is described. syn-(2R,1′S)-2-(1- Dibenzylaminomethyl) epoxide (13) was used as common building block. The key step involved oxirane ring opening of 13 by the nucleophilic lithium aza-enolate of hydrazones 12a and 12b. Subsequent hydrazone hydrolysis and intramolecular reductive amination afforded the alkaloid (+)-deoxocassine and a new C-6 ethyl analogue of this substance in good yields.

Highly enantioselective access to α-dibenzylamino ketones from chiral nonracemic α-bromo α′-sulfinyl ketones by dynamic kinetic resolution: Synthesis of (2R,1′S)-2-[1-(dibenzylamino)alkyl]oxiranes

A novel and efficient synthesis of enantiomerically pure α-dibenzylamino α′-sulfinyl ketones starting from a mixture of both epimers of α-bromo α′-(R)-sulfinyl ketone has been realized through combined in situ substitution-epimerization in a so-called Dynamic Kinetic Resolution (DKR). The scope of the reaction has been examined, and four differently substituted α-(S)-dibenzylamino α′-(R)- sulfinyl ketones were obtained in good yields with excellent diastereoselectivities. The utility of these derivatives was further illustrated with a highly stereoselective synthesis of syn-(2R,1′S)-2-(1- dibenzylaminoalkyl)oxiranes.