Literature DB >> 16930067

BiBr3-initiated tandem addition/silyl-Prins reactions to 2,6-disubstituted dihydropyrans.

Yajing Lian1, Robert J Hinkle.   

Abstract

A tandem addition/silyl-Prins reaction efficiently affords cis-2,6-disubstituted dihydropyrans (DHPs) using 5 mol % of BiBr3 in CH2Cl2. The reaction occurs between delta-triethylsilyloxyvinyltrimethylsilanes and a variety of aldehydes to give good to excellent isolated yields of DHPs. The diastereoselectivities in the crude products are significantly affected by aldehyde substitution with electron-rich aldehydes, providing 2-3:1 (cis:trans) and neutral (or electron-poor) aldehydes affording dr > or = 19:1 (cis:trans).

Entities:  

Year:  2006        PMID： 16930067     DOI： 10.1021/jo060738k

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  6 in total

1.  Bi(OTf)3-, TfOH-, and TMSOTf-mediated, one-pot epoxide rearrangement, addition, and intramolecular silyl-modified Sakurai (ISMS) cascade toward dihydropyrans: comparison of catalysts and role of Bi(OTf)3.

Authors:  R Frederick Lambert; Robert J Hinkle; Stephen E Ammann; Yajing Lian; Jia Liu; Shane E Lewis; Robert D Pike
Journal:  J Org Chem       Date:  2011-10-25       Impact factor: 4.354

2.  Synthesis of 2,6-disubstituted dihydropyrans via an efficient BiBr(3)-initiated three component, one-pot cascade.

Authors:  Robert J Hinkle; Yajing Lian; Lee C Speight; Heather E Stevenson; Melissa M Sprachman; Lauren A Katkish; M Christa Mattern
Journal:  Tetrahedron       Date:  2009-08-22       Impact factor: 2.457

3.  Bi(OTf)(3)-Catalyzed 5-Exo-Trig Cyclization via Halide Activation.

Authors:  Ryuji Hayashi; Gregory R Cook
Journal:  Tetrahedron Lett       Date:  2008       Impact factor: 2.415

4.  Palladium-catalyzed reactions of arylindium reagents prepared directly from aryl iodides and indium metal.

Authors:  Vardan Papoian; Thomas Minehan
Journal:  J Org Chem       Date:  2008-08-22       Impact factor: 4.354

5.  Total Synthesis of Pulvomycin D.

Authors:  Lukas Fritz; Sebastian Wienhold; Sabrina Hackl; Thorsten Bach
Journal:  Chemistry       Date:  2021-12-07       Impact factor: 5.020

6.  Synthesis and biological evaluation of QRSTUVWXYZA' domains of maitotoxin.

Authors:  K C Nicolaou; Philipp Heretsch; Tsuyoshi Nakamura; Anna Rudo; Michio Murata; Keiichi Konoki
Journal:  J Am Chem Soc       Date:  2014-11-06       Impact factor: 15.419
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.