Literature DB >> 19072097

Annulations of enantioenriched allenylsilanes with in situ generated iminium ions: stereoselective synthesis of diverse heterocycles.

Ryan A Brawn1, James S Panek.   

Abstract

Highly enantioenriched allenylsilanes participate in Lewis acid mediated annulations with in situ generated iminium ions derived from tert-butyl carbamate and methyl carbamate to selectively form functionalized 4,5-dihydropyrroles and 4,5-dihyrooxazines, respectively. The dihydropyrrole products were further elaborated in a stereocontrolled vinylsilane terminated cyclization with in situ generated oxonium ions, resulting in pyranopyrroles.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19072097      PMCID： PMC3164280          DOI： 10.1021/ol802618p

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


  12 in total

1.  Stereoselective synthesis of stereotriad subunits of polyketides through additions of nonracemic allenylsilanes to (R)- and (S)-2-methyl-3-oxygenated propanals

Authors: 
Journal:  J Org Chem       Date:  2000-01-28       Impact factor: 4.354

2.  Catalytic asymmetric synthesis of piperidine derivatives through the [4 + 2] annulation of imines with allenes.

Authors:  Ryan P Wurz; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2005-09-07       Impact factor: 15.419

3.  Some typical advances in the synthetic applications of allenes.

Authors:  Shengming Ma
Journal:  Chem Rev       Date:  2005-07       Impact factor: 60.622

4.  Small-molecule inhibitors of protein geranylgeranyltransferase type I.

Authors:  Sabrina Castellano; Hannah D G Fiji; Sape S Kinderman; Masaru Watanabe; Pablo de Leon; Fuyuhiko Tamanoi; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2007-04-17       Impact factor: 15.419

5.  Three-component, room temperature crotylation catalyzed by solid-supported Brønsted acid: enantioselective synthesis of homoallylic carbamates.

Authors:  Darren J Lipomi; James S Panek
Journal:  Org Lett       Date:  2005-10-13       Impact factor: 6.005

6.  Cu(I)-catalyzed enantioselective [3 + 2] cycloaddition reaction of 1-alkylallenylsilane with alpha-imino ester: asymmetric synthesis of dehydroproline derivatives.

Authors:  Kazunori Daidouji; Kohei Fuchibe; Takahiko Akiyama
Journal:  Org Lett       Date:  2005-03-17       Impact factor: 6.005

7.  Stereoselective synthesis of functionalized pyrrolidines via a [3 + 2]-annulation of N-Ts-alpha-amino aldehydes and 1,3-Bis(silyl)propenes.

Authors:  Per Restorp; Andreas Fischer; Peter Somfai
Journal:  J Am Chem Soc       Date:  2006-10-04       Impact factor: 15.419

8.  Silicon-directed oxa-Pictet-Spengler cyclization and an unusual dimerization of 2-trimethylsilanyl tryptophols.

Authors:  Xuqing Zhang; Xiaojie Li; James C Lanter; Zhihua Sui
Journal:  Org Lett       Date:  2005-05-12       Impact factor: 6.005

9.  Tuning the reaction paths in palladium(0)-catalyzed coupling-cyclization reaction of beta-amino allenes with organic halides: a substituent switch.

Authors:  Shengming Ma; Wenzhong Gao
Journal:  Org Lett       Date:  2002-08-22       Impact factor: 6.005

10.  Cooperative, highly enantioselective phosphinothiourea catalysis of imine-allene [3 + 2] cycloadditions.

Authors:  Yuan-Qing Fang; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2008-04-08       Impact factor: 15.419
View more
  1 in total

1.  Synthesis of enantioenriched homopropargylic sulfonamides by a three component reaction of aldehydes, sulfonamides, and chiral allenylsilanes.

Authors:  Ryan A Brawn; James S Panek
Journal:  Org Lett       Date:  2009-10-01       Impact factor: 6.005
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.