Literature DB >> 19382782

Alkylidenesilacyclopropanes derived from allenes: applications to the selective synthesis of triols and homoallylic alcohols.

Kay M Buchner1, Timothy B Clark, Janice M N Loy, Thong X Nguyen, K A Woerpel.   

Abstract

Several alkylidenesilacyclopropanes were prepared by silver-mediated silylene transfer to allenes. Oxasilacyclopentanes derived from allenes were prepared with high regio- and diastereoselectivity by a two-step, one-flask silacyclopropanation/carbonyl insertion reaction. Triols and homoallylic alcohols were formed diastereoselectively by functionalizing the oxasilacyclopentanes. An optically active allene (>98% ee) was utilized to synthesize an enantiopure homoallylic alcohol in 96% ee.

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Year:  2009        PMID： 19382782      PMCID： PMC2705192          DOI： 10.1021/ol900456v

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


  13 in total

1.  Synthesis of Methylene- and Alkylidenecyclopropane Derivatives.

Authors:  Alberto Brandi; Andrea Goti
Journal:  Chem Rev       Date:  1998-04-02       Impact factor: 60.622

2.  Total synthesis of (-)-dictyostatin.

Authors:  Gregory W O'Neil; Andrew J Phillips
Journal:  J Am Chem Soc       Date:  2006-04-26       Impact factor: 15.419

3.  Gold-catalyzed intermolecular hydroamination of allenes with arylamines and resulting high chirality transfer.

Authors:  Naoko Nishina; Yoshinori Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2006-05-12       Impact factor: 15.336

4.  Formation and reactivity of silacyclopropenes derived from siloxyalkynes: stereoselective formation of 1,2,4-triols.

Authors:  Timothy B Clark; K A Woerpel
Journal:  Org Lett       Date:  2006-08-31       Impact factor: 6.005

5.  Chiral nonracemic alpha-alkylidene and alpha-silylidene cyclopentenones from chiral allenes using an intramolecular allenic Pauson-Khand-type cycloaddition.

Authors:  Kay M Brummond; Angela D Kerekes; Honghe Wan
Journal:  J Org Chem       Date:  2002-07-26       Impact factor: 4.354

6.  Total synthesis of (-)- and (+)-membrenone C.

Authors:  James A Marshall; Keith C Ellis
Journal:  Org Lett       Date:  2003-05-15       Impact factor: 6.005

7.  Studies on Pd(II)-catalyzed coupling-cyclization of alpha- or beta-amino allenes with allylic halides.

Authors:  Shengming Ma; Fei Yu; Wenzhong Gao
Journal:  J Org Chem       Date:  2003-07-25       Impact factor: 4.354

8.  Boron-mediated aldol reaction of carboxylic esters.

Authors:  Atsushi Abiko
Journal:  Acc Chem Res       Date:  2004-06       Impact factor: 22.384

9.  Mechanism of di-tert-butylsilylene transfer from a silacyclopropane to an alkene.

Authors:  Tom G Driver; K A Woerpel
Journal:  J Am Chem Soc       Date:  2003-09-03       Impact factor: 15.419

10.  Formation and utility of oxasilacyclopentenes derived from functionalized alkynes.

Authors:  Timothy B Clark; K A Woerpel
Journal:  J Am Chem Soc       Date:  2004-08-11       Impact factor: 15.419
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  2 in total

1.  Silylene transfer to allylic sulfides: formation of substituted silacyclobutanes.

Authors:  Bryan J Ager; Laura E Bourque; Kay M Buchner; K A Woerpel
Journal:  J Org Chem       Date:  2010-08-20       Impact factor: 4.354

2.  Palladium- and Nickel-Catalyzed Carbon-Carbon Bond Insertion Reactions with Alkylidenesilacyclopropanes.

Authors:  Kay M Buchner; K A Woerpel
Journal:  Organometallics       Date:  2010-03-03       Impact factor: 3.876
  2 in total

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