Literature DB >> 17078681

Powerful Ti-crossed Claisen condensation between ketene silyl acetals or thioacetals and acid chlorides or acids.

Akira Iida1, Syogo Nakazawa, Tomohito Okabayashi, Atsushi Horii, Tomonori Misaki, Yoo Tanabe.   

Abstract

[Structure: see text] A powerful Ti-crossed Claisen condensation between ketene silyl acetals (KSAs) and acid chlorides was successfully performed to give alpha-monoalkylated esters and thermodynamically unfavorable (less accessible) alpha,alpha-dialkylated beta-keto esters in good yield (46 examples; 41-98% yield). A closely related reaction between ketene silyl thioacetals (KSTAs) and acid chlorides also proceeded smoothly to give alpha-monoalkylated and alpha,alpha-dialkylated beta-keto thioesters (21 examples; 61-97% yield). The present protocol was extended to the direct condensation of KSAs with carboxylic acids (14 examples; 71-97% yield).

Entities:  

Year:  2006        PMID： 17078681     DOI： 10.1021/ol0619361

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


  5 in total

1.  Aminyl Radical Generation via Tandem Norrish Type I Photocleavage, β-Fragmentation: Independent Generation and Reactivity of the 2'-Deoxyadenosin- N6-yl Radical.

Authors:  Liwei Zheng; Markus Griesser; Derek A Pratt; Marc M Greenberg
Journal:  J Org Chem       Date:  2017-03-20       Impact factor: 4.354

2.  Silyl glyoxylates. Conception and realization of flexible conjunctive reagents for multicomponent coupling.

Authors:  Gregory R Boyce; Stephen N Greszler; Jeffrey S Johnson; Xin Linghu; Justin T Malinowski; David A Nicewicz; Andrew D Satterfield; Daniel C Schmitt; Kimberly M Steward
Journal:  J Org Chem       Date:  2012-03-23       Impact factor: 4.354

3.  Remote stereoinduction in the acylation of fully substituted enolates: tandem Reformatsky/quaternary Claisen condensations of silyl glyoxylates and β-lactones.

Authors:  Stephen N Greszler; Justin T Malinowski; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2010-11-18       Impact factor: 15.419

4.  Synthesis of (-)-berkelic acid.

Authors:  Xiaoxing Wu; Jingye Zhou; Barry B Snider
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

5.  Introduction of the (-)-berkelic acid side chain and assignment of the C-22 stereochemistry.

Authors:  Xiaoxing Wu; Jingye Zhou; Barry B Snider
Journal:  J Org Chem       Date:  2009-08-21       Impact factor: 4.354
  5 in total

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