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Literature DB >> 19419211

Simple one-pot conversion of aldehydes and ketones to enals.

Petr Valenta¹, Natalie A Drucker, Jeffrey W Bode, Patrick J Walsh.

Abstract

A simple and efficient method to convert aldehydes into alpha,beta-unsaturated aldehydes with a two-carbon homologation is presented. Hydroboration of ethoxy acetylene with BH(3).SMe(2) generates tris(ethoxyvinyl) borane. Transmetalation with diethylzinc, addition to aldehydes or ketones, and acidic workup affords enals. When the addition is quenched with anilinium hydrochloride, 1,2-dithioglycol, or acetic anhydride, the unsaturated imine, dithiolane, or 1,1-diacetate is isolated in high yield. These transformations can be performed in a one-pot procedure.

Entities: Chemical

Mesh：

Substances：
Aldehydes
Ketones

Year: 2009 PMID： 19419211 PMCID： PMC2731546 DOI： 10.1021/ol9005757

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

17 in total

1. Useful enantioselective bicyclization reactions using an N-protonated chiral oxazaborolidine as catalyst.

Authors: Gang Zhou; Qi-Ying Hu; E J Corey
Journal: Org Lett Date: 2003-10-16 Impact factor: 6.005

Review 2. Asymmetric organocatalysis.

Authors: Jayasree Seayad; Benjamin List
Journal: Org Biomol Chem Date: 2005-02-09 Impact factor: 3.876

3. Catalytic asymmetric reductive Michael cyclization.

Authors: Jung Woon Yang; Maria T Hechavarria Fonseca; Benjamin List
Journal: J Am Chem Soc Date: 2005-11-02 Impact factor: 15.419

4. 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

5. Catalytic asymmetric synthesis of hydroxy enol ethers: approach to a two-carbon homologation of aldehydes.

Authors: Sang-Jin Jeon; Young K Chen; Patrick J Walsh
Journal: Org Lett Date: 2005-04-28 Impact factor: 6.005

6. A stereospecific synthesis of (+/-)-5,8-disubstituted indolizidines and (+/-)-1,4-disubstituted quinolizidines found in poison frog skins.

Authors: P Michel; A Rassat; J W Daly; T F Spande
Journal: J Org Chem Date: 2000-12-29 Impact factor: 4.354

7. N-heterocyclic carbene-catalyzed generation of homoenolates: gamma-butyrolactones by direct annulations of enals and aldehydes.

Authors: Stephanie S Sohn; Evelyn L Rosen; Jeffrey W Bode
Journal: J Am Chem Soc Date: 2004-11-10 Impact factor: 15.419

8. Catalytic Synthesis of gamma-Lactams via direct annulations of enals and N-sulfonylimines.

Authors: Ming He; Jeffrey W Bode
Journal: Org Lett Date: 2005-07-07 Impact factor: 6.005

9. Enantioselective organocatalytic amine conjugate addition.

Authors: Young K Chen; Masanori Yoshida; David W C MacMillan
Journal: J Am Chem Soc Date: 2006-07-26 Impact factor: 15.419

10. Highly enantio- and diastereoselective one-pot methods for the synthesis of halocyclopropyl alcohols.

Authors: Hun Young Kim; Luca Salvi; Patrick J Carroll; Patrick J Walsh
Journal: J Am Chem Soc Date: 2009-01-28 Impact factor: 15.419

5 in total

1. Chiral N-heterocyclic carbene-catalyzed generation of ester enolate equivalents from {alpha},{beta}-unsaturated aldehydes for enantioselective Diels-Alder reactions.

Authors: Juthanat Kaeobamrung; Marisa C Kozlowski; Jeffrey W Bode
Journal: Proc Natl Acad Sci U S A Date: 2010-10-25 Impact factor: 11.205

5. DualPhos: a versatile, chemoselective reagent for two-carbon aldehyde to latent (E)-alkenal homologation and application in the total synthesis of phomolide G.

Authors: David McLeod; James McNulty
Journal: R Soc Open Sci Date: 2016-11-23 Impact factor: 2.963