Literature DB >> 34609884

Palladium-Catalyzed, Enantioselective Desymmetrization of N-Acylaziridines with Indoles.

Kinney Van Hecke1, Tyler R Benton1, Michael Casper1, Dustin Mauldin1, Brandon Drake1, Jeremy B Morgan1.   

Abstract

Ring opening reactions of meso-aziridines generate chiral amine derivatives where the control of stereochemistry is possible through enantioselective catalysis. We report the use of a diphosphine-palladium(II) catalyst for the highly enantioselective desymmetrization of N-acylaziridines with indoles. The β-tryptamine products are isolated in moderate to high yield across a range of indole and aziridine substitution patterns. The synthetic utility of β-tryptamine products is demonstrated by conversion to the brominated pyrroloindoline derivative.

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Year:  2021        PMID： 34609884      PMCID： PMC9022218          DOI： 10.1021/acs.orglett.1c02914

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.072


  25 in total

1.  Mechanistic insights into the stereocontrolled synthesis of hexahydropyrrolo[2,3-b]indoles by electrophilic activation of tryptophan derivatives.

Authors:  Carlos Silva López; Carlos Pérez-Balado; Paula Rodríguez-Graña; Angel R de Lera
Journal:  Org Lett       Date:  2007-12-11       Impact factor: 6.005

2.  Enantiospecific total synthesis of the hapalindoles, fischerindoles, and welwitindolinones via a redox economic approach.

Authors:  Jeremy M Richter; Yoshihiro Ishihara; Takeshi Masuda; Brandon W Whitefield; Tomás Llamas; Antti Pohjakallio; Phil S Baran
Journal:  J Am Chem Soc       Date:  2008-12-31       Impact factor: 15.419

Review 3.  Aziridines and aziridinium ions in the practical synthesis of pharmaceutical intermediates--a perspective.

Authors:  Vilas H Dahanukar; Ilia A Zavialov
Journal:  Curr Opin Drug Discov Devel       Date:  2002-11

Review 4.  Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C-N Bonds in Total Synthesis.

Authors:  Artur K Mailyan; John A Eickhoff; Anastasiia S Minakova; Zhenhua Gu; Ping Lu; Armen Zakarian
Journal:  Chem Rev       Date:  2016-03-25       Impact factor: 60.622

5.  Catalytic Asymmetric Reactions of α-Isocyanoacetates and meso-Aziridines Mediated by an in-Situ-Generated Magnesium Catalytic Method.

Authors:  Dan Li; Linqing Wang; Haiyong Zhu; Lutao Bai; Yuling Yang; Minmin Zhang; Dongxu Yang; Rui Wang
Journal:  Org Lett       Date:  2019-05-30       Impact factor: 6.005

6.  Structure, bioactivity and synthesis of natural products with hexahydropyrrolo[2,3-b]indole.

Authors:  Pau Ruiz-Sanchis; Svetlana A Savina; Fernando Albericio; Mercedes Álvarez
Journal:  Chemistry       Date:  2011-01-12       Impact factor: 5.236

7.  Catalytic asymmetric construction of pyrroloindolines via an in situ generated magnesium catalyst.

Authors:  Linqing Wang; Dongxu Yang; Fengxia Han; Dan Li; Depeng Zhao; Rui Wang
Journal:  Org Lett       Date:  2014-12-31       Impact factor: 6.005

8.  Highly enantioselective ring-opening reactions of aziridines with indole and its application in the building of C3-halogenated pyrroloindolines.

Authors:  Dongxu Yang; Linqing Wang; Fengxia Han; Dan Li; Depeng Zhao; Yiming Cao; Yunxia Ma; Weidong Kong; Quantao Sun; Rui Wang
Journal:  Chemistry       Date:  2014-10-28       Impact factor: 5.236

9.  Divergent Synthesis of Enantioenriched β-Functional Amines via Desymmetrization of meso-Aziridines with Isocyanides.

Authors:  Xiangqiang Li; Qian Xiong; Mingming Guan; Shunxi Dong; Xiaohua Liu; Xiaoming Feng
Journal:  Org Lett       Date:  2019-07-24       Impact factor: 6.005

10.  Mechanistic studies on the catalytic asymmetric Mannich-type reaction with dihydroisoquinolines and development of oxidative Mannich-type reactions starting from tetrahydroisoquinolines.

Authors:  Christian Dubs; Yoshitaka Hamashima; Naoki Sasamoto; Thomas M Seidel; Shoko Suzuki; Daisuke Hashizume; Mikiko Sodeoka
Journal:  J Org Chem       Date:  2008-06-26       Impact factor: 4.354
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