Literature DB >> 23848568

One-pot asymmetric synthesis of seven-membered carbocycles cyclohepta[b]indoles via a sequential organocatalytic Michael/double Friedel-Crafts alkylation reaction.

Nitin S Dange1, Bor-Cherng Hong, Chih-Ching Lee, Gene-Hsiang Lee.   

Abstract

A new method has been developed for the enantioselective synthesis of highly functionalized cyclohepta[b]indoles with high enantioselectivity (up to 96% ee). The process combines an enantioselective organocatalytic Michael addition and a highly efficient double Friedel-Crafts reaction sequence in one pot with good yields and stereoselectivity. The structures and absolute configurations of the products were confirmed by X-ray analysis.

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Year:  2013        PMID: 23848568     DOI: 10.1021/ol4016749

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  2 in total

1.  Streocontrolled construction of six vicinal stereogenic centers on spiropyrazolones via organocascade Michael/Michael/1,2-addition reactions.

Authors:  Pankaj Chauhan; Suruchi Mahajan; Charles C J Loh; Gerhard Raabe; Dieter Enders
Journal:  Org Lett       Date:  2014-05-19       Impact factor: 6.005

2.  Combining silver catalysis and organocatalysis: a sequential Michael addition/hydroalkoxylation one-pot approach to annulated coumarins.

Authors:  Daniel Hack; Pankaj Chauhan; Kristina Deckers; Gary N Hermann; Lucas Mertens; Gerhard Raabe; Dieter Enders
Journal:  Org Lett       Date:  2014-09-24       Impact factor: 6.005

  2 in total

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