Literature DB >> 11263891

The asymmetric catalytic aldol reaction of allenolates with aldehydes using n-fluoroacyl oxazaborolidine as the catalyst.

G Li1, H X Wei, B S Phelps, D W Purkiss, S H Kim.   

Abstract

The asymmetric catalytic aldol reaction of silyl allenolates with aldehydes has been achieved by using N-C(3)F(7)CO oxazaborolidine as the catalyst. The fluoroacyl group of the catalyst was found to be crucial for control of enantioselectivity. The reaction provides the first enantioselective approach to beta-halo Baylis-Hillman-type adducts.

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Year:  2001        PMID: 11263891     DOI: 10.1021/ol000377+

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


  7 in total

1.  Asymmetric catalytic N-phosphonyl imine chemistry: the use of primary free amino acids and Et2AlCN for asymmetric catalytic Strecker reaction.

Authors:  Parminder Kaur; Suresh Pindi; Walter Wever; Trideep Rajale; Guigen Li
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354

2.  Novel approach to multifunctionalized homoallylic alcohols via regioselective ring opening of aryl oxiranes with 3-iodo allenoates.

Authors:  Adiseshu Kattuboina; Parminder Kaur; Cody Timmons; Guigen Li
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

3.  Total synthesis and absolute stereochemical assignment of kibdelone C.

Authors:  David L Sloman; Jeffrey W Bacon; John A Porco
Journal:  J Am Chem Soc       Date:  2011-06-15       Impact factor: 15.419

4.  Lewis acid-catalyzed conjugate additions of silyloxyallenes: a selective solution to the intermolecular Rauhut-Currier problem.

Authors:  Troy E Reynolds; Michael S Binkley; Karl A Scheidt
Journal:  Org Lett       Date:  2008-05-14       Impact factor: 6.005

5.  N-heterocyclic carbene-initiated alpha-acylvinyl anion reactivity: additions of alpha-hydroxypropargylsilanes to aldehydes.

Authors:  Troy E Reynolds; Charlotte A Stern; Karl A Scheidt
Journal:  Org Lett       Date:  2007-06-01       Impact factor: 6.005

6.  Cascade cyclizations of acyclic and macrocyclic alkynones: studies toward the synthesis of phomactin A.

Authors:  Jennifer Ciesielski; Vincent Gandon; Alison J Frontier
Journal:  J Org Chem       Date:  2013-06-10       Impact factor: 4.354

7.  Catalytic enantioselective alpha-acylvinyl anion reactions of silyloxyallenes.

Authors:  Troy E Reynolds; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

  7 in total

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