Literature DB >> 25533617

Regiodivergent addition of phenols to allylic oxides: control of 1,2- and 1,4-additions for cyclitol synthesis.

Matthew J Moschitto1, David N Vaccarello, Chad A Lewis.   

Abstract

Control of 1,2- and 1,4-addition of substituted phenols to allylic oxides is achieved by intercepting palladium π-allyl complexes. The interconversion of palladium complexes results in the total synthesis of MK 7607, cyathiformine B type, streptol, and a new cyclitol.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbasugars; homogeneous catalysis; palladium; regiodivergence; synthetic methods

Mesh：

Substances：

Year:  2014        PMID： 25533617      PMCID： PMC4347901          DOI： 10.1002/anie.201410228

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  11 in total

1.  Atom economic asymmetric creation of quaternary carbon: regio- and enantioselective reactions of a vinylepoxide with a carbon nucleophile.

Authors:  B M Trost; C Jiang
Journal:  J Am Chem Soc       Date:  2001-12-26       Impact factor: 15.419

2.  Asymmetric Transition Metal-Catalyzed Allylic Alkylations.

Authors:  Barry M. Trost; David L. Van Vranken
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

3.  Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.

Authors:  Barry M Trost; Matthew L Crawley
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

Review 4.  Synthesis and conformational and biological aspects of carbasugars.

Authors:  Odón Arjona; Ana M Gómez; J Cristóbal López; Joaquín Plumet
Journal:  Chem Rev       Date:  2007-05       Impact factor: 60.622

5.  Palladium-mediated regiodivergent kinetic resolution.

Authors:  G R Cook; S Sankaranarayanan
Journal:  Org Lett       Date:  2001-11-01       Impact factor: 6.005

6.  Solvent-dependent dynamic kinetic asymmetric transformation/kinetic resolution in molybdenum-catalyzed asymmetric allylic alkylations.

Authors:  David L Hughes; Michael Palucki; Nobuyoshi Yasuda; Robert A Reamer; Paul J Reider
Journal:  J Org Chem       Date:  2002-05-03       Impact factor: 4.354

7.  Facile and efficient synthesis of naturally occurring carbasugars (+)-pericosines A and C.

Authors:  Yoshihide Usami; Marie Ohsugi; Koji Mizuki; Hayato Ichikawa; Masao Arimoto
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

8.  Synthesis of (-)-pericosine B, the antipode of the cytotoxic marine natural product.

Authors:  Yoshihide Usami; Kentaro Suzuki; Koji Mizuki; Hayato Ichikawa; Masao Arimoto
Journal:  Org Biomol Chem       Date:  2008-11-13       Impact factor: 3.876

9.  Structure-based rationale for selectivity in the asymmetric allylic alkylation of cycloalkenyl esters employing the Trost 'Standard Ligand' (TSL): isolation, analysis and alkylation of the monomeric form of the cationic eta(3)-cyclohexenyl complex [(eta(3)-c-C6H9)Pd(TSL)]+.

Authors:  Craig P Butts; Emane Filali; Guy C Lloyd-Jones; Per-Ola Norrby; David A Sale; York Schramm
Journal:  J Am Chem Soc       Date:  2009-07-29       Impact factor: 15.419

10.  Callipeltoside a: total synthesis, assignment of the absolute and relative configuration, and evaluation of synthetic analogues.

Authors:  Barry M Trost; Janet L Gunzner; Olivier Dirat; Young H Rhee
Journal:  J Am Chem Soc       Date:  2002-09-04       Impact factor: 15.419
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  4 in total

1.  Regiodivergent addition of phenols to allylic oxides.

Authors:  David N Vaccarello; Matthew J Moschitto; Chad A Lewis
Journal:  J Org Chem       Date:  2015-05-01       Impact factor: 4.354

2.  Pd- η3 -C6H9 complexes of the Trost modular ligand: high nuclearity columnar aggregation controlled by concentration, solvent and counterion.

Authors:  Daugirdas Tomas Racys; Julian Eastoe; Per-Ola Norrby; Isabelle Grillo; Sarah E Rogers; Guy C Lloyd-Jones
Journal:  Chem Sci       Date:  2015-07-15       Impact factor: 9.825

3.  Synthesis of Natural O-Linked Carba-Disaccharides, (+)- and (-)-Pericosine E, and Their Analogues as α-Glucosidase Inhibitors.

Authors:  Yoshihide Usami; Koji Mizuki; Rikiya Kawahata; Makio Shibano; Atsuko Sekine; Hiroki Yoneyama; Shinya Harusawa
Journal:  Mar Drugs       Date:  2017-01-23       Impact factor: 5.118

4.  Novel Stereoselective Syntheses of (+)-Streptol and (-)-1-epi-Streptol Starting from Naturally Abundant (-)-Shikimic Acid.

Authors:  Xing-Liang Zhu; Yong-Qiang Luo; Lei Wang; Yong-Kang Huang; Yun-Gang He; Wen-Jing Xie; Shi-Ling Liu; Xiao-Xin Shi
Journal:  ACS Omega       Date:  2021-06-23
  4 in total

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