Literature DB >> 24205937

Synthesis of β-hydroxy-α-haloesters through super silyl ester directed syn-selective aldol reaction.

Susumu Oda1, Hisashi Yamamoto.   

Abstract

Super silyl haloesters including chloro- and bromoacetate were synthesized and utilized for aldol reactions to give syn-β-hydroxy-α-haloacetates in good yields with high diastereoselectivities. β-Hydroxy-α-fluoroacetate was obtained by lithiation of super silyl bromofluoroacetate. Sequential Darzens reactions provided cis-glycidic esters in moderate yields.

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Year:  2013        PMID: 24205937      PMCID: PMC3946542          DOI: 10.1021/ol402928p

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


  34 in total

1.  Strategies for catalytic asymmetric electrophilic alpha halogenation of carbonyl compounds.

Authors:  Martin Oestreich
Journal:  Angew Chem Int Ed Engl       Date:  2005-04-15       Impact factor: 15.336

2.  Design of organocatalysts for asymmetric direct syn-aldol reactions.

Authors:  Xiao-Ying Xu; Yan-Zhao Wang; Liu-Zhu Gong
Journal:  Org Lett       Date:  2007-10-11       Impact factor: 6.005

3.  Rapid, one-pot synthesis of β-siloxy-α-haloaldehydes.

Authors:  Jakub Saadi; Matsujiro Akakura; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2011-08-18       Impact factor: 15.419

Review 4.  The unique role of halogen substituents in the design of modern agrochemicals.

Authors:  Peter Jeschke
Journal:  Pest Manag Sci       Date:  2010-01       Impact factor: 4.845

5.  Synthesis of undecachlorosulfolipid A: re-evaluation of the nominal structure.

Authors:  Christian Nilewski; Nicholas R Deprez; Thomas C Fessard; Dong Bo Li; Roger W Geisser; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-08       Impact factor: 15.336

Review 6.  Chlorosulfolipids: structure, synthesis, and biological relevance.

Authors:  D Karl Bedke; Christopher D Vanderwal
Journal:  Nat Prod Rep       Date:  2010-12-02       Impact factor: 13.423

7.  Enantioselective dichlorination of allylic alcohols.

Authors:  K C Nicolaou; Nicholas L Simmons; Yongcheng Ying; Philipp M Heretsch; Jason S Chen
Journal:  J Am Chem Soc       Date:  2011-05-10       Impact factor: 15.419

8.  Total synthesis of a chlorosulpholipid cytotoxin associated with seafood poisoning.

Authors:  Christian Nilewski; Roger W Geisser; Erick M Carreira
Journal:  Nature       Date:  2009-01-29       Impact factor: 49.962

Review 9.  α-Haloaldehydes: versatile building blocks for natural product synthesis.

Authors:  Robert Britton; Baldip Kang
Journal:  Nat Prod Rep       Date:  2013-02       Impact factor: 13.423

10.  β-Siloxy-α-haloketones through highly diastereoselective single and double mukaiyama aldol reactions.

Authors:  Jakub Saadi; Hisashi Yamamoto
Journal:  Chemistry       Date:  2013-02-19       Impact factor: 5.236

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