158362-66-4

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 128726-47-6 (+)-(S)-6-hydroxymethyl-2-piperidinone 
• 158414-69-8 (-)-(S)-6-oxo-2-piperidinecarboxylic acid methyl ester 
• 2483-48-9 (+)-(S)-N₂,N₆-bis[(1,1-dimethylethoxy)carbonyl]-lysine methyl ester 
• 97347-42-7 (+)-(S)-N₂,N₆-bis[(1,1-dimethylethoxy)carbonyl]-6-oxo-lysine methyl ester 

Downstream Products

• 158362-68-6 (3R,8aS)-3-Phenyl-6-phenylselanyl-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-5-one 
• 705947-41-7 (2R,5S)-8-ethoxycarbonyl-9-oxo-2-phenyl-1-aza-3-oxabicyclo[4.3.0]nonane 
• 158362-67-5 (+)-(2R,5S)-1-aza-3-oxa-9-oxo-2-phenyl-8,8-bis(phenylselenenyl)bicyclo[4.3.0]nonane 

Relevant academic research and scientific papers

A SHORT APPROACH TO FUNCTIONALISED HOMOCHIRAL PIPERIDINONES

The preparation of homochiral lactam 4 in 5 steps from (S)-lysine is described.Conversion to bicyclic O,N-acetal 5 provides a useful template for further elaboration to highly substituted piperidinones with excellent diastereoselectivity.

Enantiopure bicyclic piperidinones: Stereoselectivity in lactam enolate alkylations

The synthesis and alkylation of [4.3.0]-bicyclic lactams, derived from 6-oxopipecolic acid, have been investigated. Alkylation can proceed with predominantly exo-diastereoselectivity, but the efficiency of this process depends on the substitution at the hemiaminal ether system. These products can be readily deprotected to give substituted hydroxymethyl lactams in good yield.

Diastereoselectivity in the alkylations of bicyclic piperidinones

The synthesis of substituted [4.3.0] bicyclic lactams derived from 6- oxo-2-hydroxymethylpiperidine is described. The enolate derived flora these systems can be alkylated with a range of reactive electrophiles; the diastereoselectivity which can be achieved depends on the substitution pattern of the oxazolidine ring system and the nature of the alkylating reagent, and can vary from 1:1 to as much as 10:1.