185899-63-2

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 172985-52-3 3,4-bismethylene-1,6-hexanediol 
• 83767-31-1 3,4-dimethylenehexanedioic acid diethyl ester 
• 365223-96-7 acetic acid 4-(2-acetoxy-ethyl)-3-methylene-pent-4-enyl ester 

Downstream Products

• 185899-64-3 4,5-dimethylene-2,3,6,7-tetrahydro-azep-1-yl-p-tolylsulfone 
• 185899-65-4 1,1-dichloro-9-methylene-6-azaspiro[2,6]non-6-yl-p-tolylsulfone 

Relevant academic research and scientific papers

Copper-Catalyzed Dehydrogenative Diels-Alder Reaction

A practical and effective copper-catalyzed dehydrogenative Diels-Alder reaction of gem-diesters and ketone with dienes has been established. The active dienophiles were generated in situ via a radical-based dehydrogenation process, which reacted with a wide variety of dienes to afford various polysubstituted cyclohexene derivatives in good to excellent yields.

Synthesis of benzocycloheptene-based amino acid derivatives via a [4+2] cycloaddition reaction as a key step

The seven-membered diene 5 is prepared from 2-butyne-1,4-diol using double orthoester Claisen rearrangement reaction as a key step. The Diels-Alder reaction of the diene 5 with various dienophiles followed by oxidation delivered the benzocycloheptene-based α-amino acid derivatives in very good yields.

Synthesis of constrained α-amino acid derivatives via diels-alder approach

Synthesis of new five and seven membered outer ring diene building blocks containing α-amino acid moiety and their usage in the preparation of the constrained amino acid derivatives is described.