401519-99-1

Upstream product

• 111-71-7 heptanal 
• 98-59-9 p-toluenesulfonyl chloride 
• 401519-98-0 (2R,3R)-2-methylnonane-1,3-diol 
• 439278-20-3 (S)-4-benzyl-3-((2S,3R)-3-hydroxy-2-methylnonanoyl)-1,3-thiazolidine-2-thione 
• 401519-97-9 (S)-4-benzyl-3-((2S,3R)-3-hydroxy-2-methylnonanoyl)1,3-oxazolidin-2-one 

Relevant academic research and scientific papers

Synthesis of natural fragrant molecules cis-3-methyl-4-decanolide and aerangis lactone. General enantioselective routes to beta,gamma-cis-disubstituted gamma-lactones and gamma,delta-cis-disubstituted delta-lactones.

General enantioselective routes to 3,4-cis-dialkyl substituted gamma-lactones and 4,5-cis-dialkyl substituted delta-lactones using TiCl(4)-mediated Evans asymmetric aldolization as the key step are reported. The syntheses are exemplified with two natural fragrant molecules, cis-3-methyl-4-decanolide (1) and aerangis lactone (2). The (R,R) steroegenic centers were established using (S)-phenylalanine-derived 2-oxazolidinone or thiazolidinethione as chiral auxiliary, whereas the (S,S) ones were constructed with auxiliary prepared from (R)-phenylglycine. NaBH(4)/CaCl(2)/THF in the presence of a small amount of EtOH was introduced as a new effective method for reductive cleavage of chiral oxazolidinone auxiliaries. Previously unknown, tricky concentration effects were observed during the monotosylation of diol 7 and BOM protection of Evans aldol 23.

An expeditious access to enantiomerically pure cis-dialkyl-substituted γ- and δ-lactones

A facile general route to enantiomerically pure 3,4-cis-dialkyl-substituted γ-lactones and 4,5-cis-dialkyl-substituted δ-lactones by TiCl4-mediated Evans asymmetric aldolization as the key step is exemplified by synthesis of cis-(3R,4R)-3-methy