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Literature DB >> 21815682

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

Jakub Saadi¹, Matsujiro Akakura, Hisashi Yamamoto.

Abstract

The Mukaiyama cross-aldol reaction of α-fluoro-, α-chloro-, and α-bromoacetaldehyde-derived (Z)-tris(trimethylsilyl)silyl enol ethers is described, furnishing anti-β-siloxy-α-haloaldehydes. A highly diastereoselective, one-pot, sequential double-aldol process is developed, affording novel β,δ-bissiloxy-α,γ-bishaloaldehydes. Reactions are catalyzed by C(6)F(5)CHTf(2) and C(6)F(5)CTf(2)AlMe(2) (0.5-1.5 mol %) and provide access to halogenated polyketide fragments.

Entities: Chemical Disease Gene

Mesh：

Substances：
Polyketides
Acetaldehyde

Year: 2011 PMID： 21815682 PMCID： PMC3181128 DOI： 10.1021/ja2066169

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

44 in total

1. Organocatalytic asymmetric alpha-bromination of aldehydes and ketones.

Authors: Søren Bertelsen; Nis Halland; Stephan Bachmann; Mauro Marigo; Alan Braunton; Karl Anker Jørgensen
Journal: Chem Commun (Camb) Date: 2005-08-30 Impact factor: 6.222

Review 2. 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

3. Mukaiyama aldol addition to alpha-chloro-substituted aldehydes. Origin of the unexpected syn selectivity.

Authors: Tessie Borg; Jakob Danielsson; Peter Somfai
Journal: Chem Commun (Camb) Date: 2010-01-07 Impact factor: 6.222

Review 4. 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

5. Enantioselective organo-cascade catalysis.

Authors: Yong Huang; Abbas M Walji; Catharine H Larsen; David W C MacMillan
Journal: J Am Chem Soc Date: 2005-11-02 Impact factor: 15.419

6. 1-Amino-3-siloxy-1,3-butadienes: Highly Reactive Dienes for the Diels-Alder Reaction.

Authors: Sergey A. Kozmin; Jacob M. Janey; Viresh H. Rawal
Journal: J Org Chem Date: 1999-04-30 Impact factor: 4.354

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. Asymmetric induction in methyl ketone aldol additions to alpha-alkoxy and alpha,beta-bisalkoxy aldehydes: a model for acyclic stereocontrol.

Authors: David A Evans; Victor J Cee; Sarah J Siska
Journal: J Am Chem Soc Date: 2006-07-26 Impact factor: 15.419

9. Enantioselective α-Chlorination of Aldehydes with Recyclable Fluorous (S)-Pyrrolidine-Thiourea Bifunctional Organocatalyst.

Authors: Liang Wang; Chun Cai; Dennis P Curran; Wei Zhang
Journal: Synlett Date: 2010-01-01 Impact factor: 2.454

10. 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

9 in total

1. Rapid and stereochemically flexible synthesis of polypropionates: super-silyl-governed aldol cascades.

Authors: Patrick B Brady; Hisashi Yamamoto
Journal: Angew Chem Int Ed Engl Date: 2012-01-17 Impact factor: 15.336

2. The supersilyl group as a carboxylic acid protecting group: application to highly stereoselective aldol and Mannich reactions.

Authors: Jiajing Tan; Matsujiro Akakura; Hisashi Yamamoto
Journal: Angew Chem Int Ed Engl Date: 2013-05-29 Impact factor: 15.336

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

1. Organocatalytic asymmetric alpha-bromination of aldehydes and ketones.

Review 2. The unique role of halogen substituents in the design of modern agrochemicals.

3. Mukaiyama aldol addition to alpha-chloro-substituted aldehydes. Origin of the unexpected syn selectivity.

Review 4. Chlorosulfolipids: structure, synthesis, and biological relevance.

5. Enantioselective organo-cascade catalysis.

6. 1-Amino-3-siloxy-1,3-butadienes: Highly Reactive Dienes for the Diels-Alder Reaction.

7. Enantioselective dichlorination of allylic alcohols.

8. Asymmetric induction in methyl ketone aldol additions to alpha-alkoxy and alpha,beta-bisalkoxy aldehydes: a model for acyclic stereocontrol.

9. Enantioselective α-Chlorination of Aldehydes with Recyclable Fluorous (S)-Pyrrolidine-Thiourea Bifunctional Organocatalyst.

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

1. Rapid and stereochemically flexible synthesis of polypropionates: super-silyl-governed aldol cascades.

2. The supersilyl group as a carboxylic acid protecting group: application to highly stereoselective aldol and Mannich reactions.

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

4. Generation of organolithium compounds bearing super silyl ester and their application to Matteson rearrangement.

5. Enantioselective aldol reactions with masked fluoroacetates.

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

7. Ten years of research in Chicago.

8. Stereodivergent approach to the avermectins based on "super silyl" directed aldol reactions.

9. A highly diastereoselective "super silyl" governed aldol reaction: synthesis of α,β-dioxyaldehydes and 1,2,3-triols.