Literature DB >> 19348489

Lewis base-promoted hydrosilylation of cyclic malonates: synthesis of beta-substituted aldehydes and gamma-substituted amines.

Christopher G Frost1, Benjamin C Hartley.   

Abstract

The Lewis base-promoted hydrosilylation of cyclic malonates provides a convenient synthesis of beta-substituted aldehydes. No over-reduction to the primary alcohol is observed as the aldehyde functionality is protected until a subsequent hydrolysis step. The utility of the method is demonstrated in a number of examples and further in the synthesis of gamma-substituted propylamines in a one-pot hydrosilylation/reductive amination process.

Entities:  

Year:  2009        PMID: 19348489     DOI: 10.1021/jo900390d

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  2 in total

1.  Selective synthesis of 3-hydroxy acids from Meldrum's acids using SmI2-H2O.

Authors:  Michal Szostak; Malcolm Spain; David J Procter
Journal:  Nat Protoc       Date:  2012-04-26       Impact factor: 13.491

2.  Ethylenation of aldehydes to 3-propanal, propanol and propanoic acid derivatives.

Authors:  Daniel T Payne; Yiming Zhao; John S Fossey
Journal:  Sci Rep       Date:  2017-05-11       Impact factor: 4.379

  2 in total

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