605686-10-0

Upstream product

• 930-30-3 cyclopent-2-enone 
• 2004-70-8 1-methylbuta-1,3-diene 
• 605686-10-0 7t-Methyl-(3arH,7acH)-3a,4,7,7a-tetrahydro-indanon-⁽¹⁾ 

Downstream Products

• 22643-74-9 7trans-Methyl-(3a ref H,7a trans H)-hexahydro-indanon-(1) 
• 83586-04-3 7t-Methyl-(3arH,7atH)-3a,4,7,7a-tetrahydro-indanon-⁽¹⁾ 

Relevant academic research and scientific papers

Asymmetric synthesis of chiral 1,3-diaminopropanols: Bisoxazolidine- catalyzed C-C bond formation with α-keto amides

Three high-yielding steps lead to the formation of chiral 1,3-diaminopropanols from aliphatic and aromatic α-keto amides. In this approach, a nitroaldol reaction, which is catalyzed by Cu(SO2CF 3)2 and the bisoxazolidine ligand L1, is followed by two mild reduction reactions (see scheme). Laborious protection and deprotection steps can be avoided by using this method.

Synthesis of new chiral auxiliaries for 6π-azaelectrocyclization: 4- and 7-alkyl substituted cis-1-amino-2-indanols

The synthesis of new chiral auxiliaries, 7-alkyl substituted cis-1-amino-2-indanol derivatives, was established by the Diels-Alder reaction of 1-substituted dienes with cyclopentenone followed by the asymmetric epoxidation of the resulting indene derivatives and then the Ritter reaction. These bulky cis-aminoindanol derivatives are very effective as chiral auxiliaries and nitrogen sources in the asymmetric 6π-azaelectrocyclization. The corresponding 4-alkyl derivative was also prepared using a similar method.

Development of highly stereoselective asymmetric 6π- azaelectrocyclization of conformationally flexible linear 1-azatrienes. From determination of multifunctional chiral amines, 7-alkyl cis-1-amino-2-indanols, to application as a new synthetic strategy: Formal synthesis of 20-epiuleine

The highly stereoselective asymmetric 6π-azaelectrocyclization was achieved as a general synthetic method based on the reaction between the (E)-3-carbonyl-2,4,6-trienal compounds and the (-)-7-alkyl-cis-l-amino-2-indanol derivatives which are effective chiral amines. The 7-alkyl-substituted 2-indanol moiety of the cyclized products was efficiently removed by the novel manganese dioxide oxidation under remarkably mild conditions, and the method was successfully applied to the formal synthesis of optically active 20-epiuleine.