Literature DB >> 24446703

Conjugate-base-stabilized Brønsted acids: catalytic enantioselective Pictet-Spengler reactions with unmodified tryptamine.

Nisha Mittal1, Diana X Sun, Daniel Seidel.   

Abstract

A conjugate-base-stabilized Brønsted acid facilitates catalytic enantioselective Pictet-Spengler reactions with unmodified tryptamine. The chiral carboxylic acid catalyst is readily assembled in just two steps and enables the formation of β-carbolines with up to 92% ee. Achiral acid additives or in situ Boc-protection facilitate catalyst turnover.

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Year:  2014        PMID： 24446703     DOI： 10.1021/ol403773a

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


  10 in total

1.  Chiral Thioureas Promote Enantioselective Pictet-Spengler Cyclization by Stabilizing Every Intermediate and Transition State in the Carboxylic Acid-Catalyzed Reaction.

Authors:  Rebekka S Klausen; C Rose Kennedy; Alan M Hyde; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2017-08-22       Impact factor: 15.419

2.  Tunable and Cooperative Catalysis for Enantioselective Pictet-Spengler Reaction with Varied Nitrogen-Containing Heterocyclic Carboxaldehydes.

Authors:  Yuk-Cheung Chan; Marcus H Sak; Scott A Frank; Scott J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2021-10-07       Impact factor: 15.336

3.  Screening for generality in asymmetric catalysis.

Authors:  Corin C Wagen; Spencer E McMinn; Eugene E Kwan; Eric N Jacobsen
Journal:  Nature       Date:  2022-09-01       Impact factor: 69.504

4.  Unified Synthesis of Polycyclic Alkaloids by Complementary Carbonyl Activation*.

Authors:  Guoli He; Benjamin List; Mathias Christmann
Journal:  Angew Chem Int Ed Engl       Date:  2021-05-01       Impact factor: 15.336

Review 5.  Application of the Asymmetric Pictet-Spengler Reaction in the Total Synthesis of Natural Products and Relevant Biologically Active Compounds.

Authors:  Majid M Heravi; Vahideh Zadsirjan; Masumeh Malmir
Journal:  Molecules       Date:  2018-04-18       Impact factor: 4.411

Review 6.  From Synthesis to Characterization of Site-Selective PEGylated Proteins.

Authors:  Lisandra Herrera Belén; Carlota de Oliveira Rangel-Yagui; Jorge F Beltrán Lissabet; Brian Effer; Manuel Lee-Estevez; Adalberto Pessoa; Rodrigo L Castillo; Jorge G Farías
Journal:  Front Pharmacol       Date:  2019-12-18       Impact factor: 5.810

7.  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

8.  Synthesis of tetrahydro-β-carbolines from 2-indolylmethyl azides and propargylic alcohols.

Authors:  Haiting Yin; Qin Ma; Yushan Wang; Xiaoxia Gu; Zhijun Feng; Yunjun Wu; Ming Wang; Shaoyin Wang
Journal:  RSC Adv       Date:  2021-06-01       Impact factor: 3.361

9.  Catalytic Enantioselective Pictet-Spengler Reaction of α-Ketoamides Catalyzed by a Single H-Bond Donor Organocatalyst.

Authors:  Rémi Andres; Qian Wang; Jieping Zhu
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-11       Impact factor: 16.823

Review 10.  The Pictet-Spengler Reaction Updates Its Habits.

Authors:  Andrea Calcaterra; Laura Mangiardi; Giuliano Delle Monache; Deborah Quaglio; Silvia Balducci; Simone Berardozzi; Antonia Iazzetti; Roberta Franzini; Bruno Botta; Francesca Ghirga
Journal:  Molecules       Date:  2020-01-19       Impact factor: 4.411
  10 in total

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