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Literature DB >> 21919478

Thiourea-catalyzed enantioselective iso-Pictet-Spengler reactions.

Yunmi Lee¹, Rebekka S Klausen, Eric N Jacobsen.

Abstract

A one-pot condensation of isotryptamines and aldehydes that affords enantiomerically enriched 4-substituted tetrahydro-γ-carbolines is reported. The reaction is induced by a chiral thiourea/benzoic acid dual catalyst system. Purification of the N-Boc-protected products by trituration or crystallization provides the optically pure tetrahydro-γ-carboline derivatives in a scalable and highly practical procedure.

Entities: Chemical Disease Gene

Mesh：

Substances：

Year: 2011 PMID： 21919478 PMCID： PMC3206290 DOI： 10.1021/ol202300t

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

29 in total

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Authors: Alexandre Bridoux; Régis Millet; Jean Pommery; Nicole Pommery; Jean-Pierre Henichart
Journal: Bioorg Med Chem Date: 2010-04-18 Impact factor: 3.641

2. Highly enantioselective catalytic acyl-pictet-spengler reactions.

Authors: Mark S Taylor; Eric N Jacobsen
Journal: J Am Chem Soc Date: 2004-09-01 Impact factor: 15.419

Review 3. The Pictet-Spengler reaction in nature and in organic chemistry.

Authors: Joachim Stöckigt; Andrey P Antonchick; Fangrui Wu; Herbert Waldmann
Journal: Angew Chem Int Ed Engl Date: 2011-08-09 Impact factor: 15.336

Review 4. Chemistry and biology of monoterpene indole alkaloid biosynthesis.

Authors: Sarah E O'Connor; Justin J Maresh
Journal: Nat Prod Rep Date: 2006-05-26 Impact factor: 13.423

5. Enantioselective Pictet-Spengler-type cyclizations of hydroxylactams: H-bond donor catalysis by anion binding.

Authors: Izzat T Raheem; Parvinder S Thiara; Emily A Peterson; Eric N Jacobsen
Journal: J Am Chem Soc Date: 2007-10-17 Impact factor: 15.419

6. Catalytic asymmetric Pictet-Spengler reactions via sulfenyliminium ions.

Authors: Martin J Wanner; Richard N S van der Haas; Kimberly R de Cuba; Jan H van Maarseveen; Henk Hiemstra
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

Review 7. Total synthesis and biosynthesis of the paraherquamides: an intriguing story of the biological Diels-Alder construction.

Authors: Robert Michael Williams
Journal: Chem Pharm Bull (Tokyo) Date: 2002-06 Impact factor: 1.645

8. Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands.

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Journal: J Med Chem Date: 2002-04-25 Impact factor: 7.446

9. A short synthetic route to (+)-austamide, (+)-deoxyisoaustamide, and (+)-hydratoaustamide from a common precursor by a novel palladium-mediated indole --> dihydroindoloazocine cyclization.

Authors: Phil S Baran; E J Corey
Journal: J Am Chem Soc Date: 2002-07-10 Impact factor: 15.419

10. Neuroleptic activity in 5-aryltetrahydro-gamma-carbolines.

Authors: C A Harbert; J J Plattner; W M Welch; A Weissman; B K Koe
Journal: J Med Chem Date: 1980-06 Impact factor: 7.446

11 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. A Pictet-Spengler ligation for protein chemical modification.

Authors: Paresh Agarwal; Joep van der Weijden; Ellen M Sletten; David Rabuka; Carolyn R Bertozzi
Journal: Proc Natl Acad Sci U S A Date: 2012-12-13 Impact factor: 11.205

3. Cooperative Hydrogen-Bond-Donor Catalysis with Hydrogen Chloride Enables Highly Enantioselective Prins Cyclization Reactions.

Authors: Dennis A Kutateladze; Eric N Jacobsen
Journal: J Am Chem Soc Date: 2021-11-23 Impact factor: 15.419

Review 4. Strategies That Utilize Ion Pairing Interactions to Exert Selectivity Control in the Functionalization of C-H Bonds.

Authors: James E Gillespie; Alexander Fanourakis; Robert J Phipps
Journal: J Am Chem Soc Date: 2022-09-30 Impact factor: 16.383

Review 5. Asymmetric ion-pairing catalysis.

Authors: Katrien Brak; Eric N Jacobsen
Journal: Angew Chem Int Ed Engl Date: 2012-11-28 Impact factor: 15.336