65899-50-5

Upstream product

• 21651-12-7 (E)-2,4-pentadienoic acid 
• 75-65-0 tert-butyl alcohol 
• 65899-51-6 (E)-penta-2,4-dienoyl azide 
• 4248-19-5 tert-butyl carbazate 
• 123-73-9 crotonaldehyde 

Downstream Products

• 1338468-32-8 methyl 5-((1'S,2'R)-2-(ethyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate 
• 1419351-78-2 tert-butyl ((E)-2-((2S,4R)-6-methoxy-2-phenyl-1,2,3,4-tetrahydroquinolin-4-yl)vinyl)carbamate 
• 1419351-81-7 tert-butyl (3-((2S,4S)-6-methoxy-2-phenyl-1,2,3,4-tetrahydroquinolin-4-yl)ethyl)carbamate 

Relevant academic research and scientific papers

Molecular Design of a Chiral Br?nsted Acid with Two Different Acidic Sites: Regio-, Diastereo-, and Enantioselective Hetero-Diels-Alder Reaction of Azopyridinecarboxylate with Amidodienes Catalyzed by Chiral Carboxylic Acid-Monophosphoric Acid

A chiral Br?nsted acid containing two different acidic sites, chiral carboxylic acid-monophosphoric acid 1a, was designed to be a new and effective concept in catalytic asymmetric hetero-Diels-Alder reactions of azopyridinecarboxylate with amidodienes. The multipoint hydrogen-bonding interactions among the carboxylic acid, monophosphoric acid, azopyridinecarboxylate, and amidodiene achieved high catalytic and chiral efficiency, producing substituted 1,2,3,6-tetrahydropyridazines with excellent stereocontrol in a single step. This constitutes the first example of regio-, diastereo-, and enantioselective azo-hetero-Diels-Alder reactions by chiral Br?nsted acid catalysis.

Regioselective synthesis of secondary 1,3-dienamides by successive eliminations

The regioselective synthesis of secondary 1,3-dienamides 3 (1-N-acylamino-1,3-dienes) is successfully demonstrated by regiospecific base-promoted 1,4-elimination of (Z)- or (E)-N,N-di-Boc-4-methoxy-2-buten-1-ylamine 1 followed by mono-Boc elimination in situ.

Catalytic Asymmetric Diels-Alder Reaction of Quinone Imine Ketals: A Site-Divergent Approach

The catalytic asymmetric Diels-Alder reaction of quinone imine ketals with diene carbamates catalyzed by axially chiral dicarboxylic acids is reported herein. A variety of primary and secondary alkyl-substituted quinone derivatives which have not been applied in previous asymmetric quinone Diels-Alder reactions could be employed using this method. More importantly, we succeeded in developing a strategy to divert the reaction site in unsymmetrical 3-alkyl quinone imine ketals from the inherently favored unsubstituted C=C bond to the disfavored alkyl-substituted C=C bond.

The enantioselective synthesis of tetracyclic methyllycaconitine analogues

A new enantioselective synthesis of ABEF ring analogues of methyllycaconitine has been developed using a chiral cobalt(III) salen-catalyzed Diels-Alder reaction to form the B ring. Subsequent elaboration to form the A, E and F rings was achieved by sequential Dieckmann, Mannich and Wacker-type cyclizations to afford tetracyclic analogues in 97.5% ee.