Literature DB >> 27934390

Catalytic Enantioselective Synthesis of Tetrahydocarbazoles and Exocyclic Pictet-Spengler-Type Reactions.

Casper L Hansen1, Ragnhild G Ohm1, Lasse B Olsen1, Erhad Ascic1, David Tanner1, Thomas E Nielsen1,2.   

Abstract

A synthetic strategy for the synthesis of chiral tetrahydrocarbazoles (THCAs) has been developed. The strategy relies on two types of 6-exo-trig cyclization of 3-substituted indole substrates. Enantioselective domino Friedel-Crafts-type reactions leading to THCAs can be catalyzed by chiral phosphoric acid derivatives (with up to >99% ee), and the first examples of exocyclic Pictet-Spengler reactions to form THCAs are reported.

Entities:  

Year:  2016        PMID: 27934390     DOI: 10.1021/acs.orglett.6b02718

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


  2 in total

1.  Asymmetric Synthesis of a 5,6,7,8-Tetrahydro-1,6-naphthyridine Scaffold Leading to Potent Retinoid-Related Orphan Receptor γt Inverse Agonist TAK-828F.

Authors:  Ryoji Tsuruoka; Naoki Yoshikawa; Takahiro Konishi; Mitsuhisa Yamano
Journal:  J Org Chem       Date:  2020-07-23       Impact factor: 4.354

2.  Facile Hydrogenative Deprotection of N-Benzyl Groups Using a Mixed Catalyst of Palladium and Niobic Acid-on-Carbon.

Authors:  Yuta Yamamoto; Eisho Shimizu; Kazuho Ban; Yoshiyuki Wada; Tomoteru Mizusaki; Masatoshi Yoshimura; Yukio Takagi; Yoshinari Sawama; Hironao Sajiki
Journal:  ACS Omega       Date:  2020-02-05
  2 in total

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