Literature DB >> 23459542

Facile conversion of chromane-6-triflate to chromane-6-alanines under Palladium conditions.

Daniel K Miller1.   

Abstract

Conversion of chromane-6-triflate 5 to chromane-6-dehydroalanine 9 or 10 via its Bpin-derivative 6 followed by Suzuki coupling with protected dehydroalanine bromides 7 or 8 were reported (86%). Alternatively, a palladium-catalyzed stannation of 5 with Bu6Sn2 afforded the tributyltin derivative 11, and iodination (12) followed by coupling with 13 gave chromane-6-alanine 15 (75%). Either approach constitutes a conversion from chromane-6-triflate to the corresponding protected chromane-6-alanine or its dehydro analog.

Entities:  

Keywords:  Aryl Triflate; Boronation; Palladium-catalyzed coupling; Stannylation; Suzuki coupling

Year:  2013        PMID： 23459542      PMCID： PMC3580865          DOI： 10.1016/j.tetlet.2012.11.115

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  10 in total

1.  A cobalt-catalyzed sulfonate/copper exchange for the preparation of highly functionalized electron-deficient aryl copper reagents.

Authors:  Christoph J Rohbogner; Coura R Diène; Tobias J Korn; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-01       Impact factor: 15.336

2.  Chromene chromium carbene complexes in the syntheses of naphthopyran and naphthopyrandione units present in photochromic materials and biologically active natural products.

Authors:  Manish Rawat; Victor Prutyanov; William D Wulff
Journal:  J Am Chem Soc       Date:  2006-08-30       Impact factor: 15.419

3.  Palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides.

Authors:  Xiaoqiang Shen; Alan M Hyde; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

4.  Enantiomerically pure alpha-amino acid synthesis via hydroboration-suzuki cross-coupling.

Authors:  Philip N Collier; Andrew D Campbell; Ian Patel; Tony M Raynham; Richard J K Taylor
Journal:  J Org Chem       Date:  2002-03-22       Impact factor: 4.354

5.  Much improved conditions for the Negishi cross-coupling of iodoalanine derived zinc reagents with aryl halides.

Authors:  Andrew J Ross; Hannah L Lang; Richard F W Jackson
Journal:  J Org Chem       Date:  2010-01-01       Impact factor: 4.354

6.  Efficient asymmetric synthesis of the vasopeptidase inhibitor BMS-189921.

Authors:  Janak Singh; David R Kronenthal; Mark Schwinden; Jollie D Godfrey; Rita Fox; Edward J Vawter; Bo Zhang; Thomas P Kissick; Bharat Patel; Omar Mneimne; Michael Humora; Chris G Papaioannou; Walter Szymanski; Michael K Y Wong; Chien K Chen; James E Heikes; John D DiMarco; Jun Qiu; Rajendra P Deshpande; Jack Z Gougoutas; Richard H Mueller
Journal:  Org Lett       Date:  2003-08-21       Impact factor: 6.005

7.  Synthesis of macrocyclic, potential protease inhibitors using a generic scaffold.

Authors:  Estelle Dumez; John S Snaith; Richard F W Jackson; Andrew B McElroy; John Overington; Martin J Wythes; Jane M Withka; Thomas J McLellan
Journal:  J Org Chem       Date:  2002-07-12       Impact factor: 4.354

Review 8.  Asymmetric hydrogenation using monodentate phosphoramidite ligands.

Authors:  Adriaan J Minnaard; Ben L Feringa; Laurent Lefort; Johannes G de Vries
Journal:  Acc Chem Res       Date:  2007-08-18       Impact factor: 22.384

9.  Structural determinants of selective thyromimetics.

Authors:  Hikari A I Yoshihara; James W Apriletti; John D Baxter; Thomas S Scanlan
Journal:  J Med Chem       Date:  2003-07-03       Impact factor: 7.446

10.  Chiral diphosphine and monodentate phosphorus ligands on a spiro scaffold for transition-metal-catalyzed asymmetric reactions.

Authors:  Jian-Hua Xie; Qi-Lin Zhou
Journal:  Acc Chem Res       Date:  2008-03-01       Impact factor: 22.384
  10 in total

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