99249-36-2

Upstream product

• 75-11-6 diiodomethane 
• 99249-35-1 2-methyl-2-cyclohexen-1-one cyclic (1S,2S)-1,2-bis<(benzyloxy)methyl>ethylene acetal 
• 10409-47-9 2-bromo-2-methylcyclohexanone 
• 99249-46-4 (2S,3S)-2,3-Bis-benzyloxymethyl-6-bromo-6-methyl-1,4-dioxa-spiro[4.5]decane 
• 17401-06-8 (2S,3S)-1,4-bis(benzyloxy)-2,3-butanediol 

Relevant academic research and scientific papers

HOMOCHIRAL KETALS IN ORGANIC SYNTHESIS. DIASTEREOSELECTIVE CYCLOPROPANATION OF α,β-UNSATURATED KETALS DERIVED FROM 1,4-Di-O-BENZYL-L-THREITOL

2-Cykloalken-1-one 1,4-di-O-benzyl-L-threitol ketals undergo efficient and diastereoselective cyclopropanation when treated with an excess of the Simmons-Smith reagent.For example, 2-cyclohexen-1-one 1,4-di-O-benzyl-L-threitol ketal gave in 90-98percent yield a 9:1 mixture of diastereomeric cyclopropanes as established by 62.9 MHz 13C NMR spectroscopy and by hydrolysis of the mixture to (1R,6S)-bicycloheptan-2-one.Sixteen other examples are presented which demonstrate the generality and predictability of the process for 2-cycloalken-1-one ketals, as well as an unfortunate lack of diastereoselectivity for α,β-unsaturated 1,4-di-O-benzyl-L-threitol acetals.