Literature DB >> 18181637

Super silyl group for a sequential diastereoselective aldol-polyhalomethyllithium addition reaction.

Matthew B Boxer1, Hisashi Yamamoto.   

Abstract

The super silyl group governs high diastereoselectivity and yields for a sequential aldol-polyhalomethyllithium addition reaction. This unique silyl group is necessary to obtain the diastereoselectivities associated with this sequential reaction, capable of generating two new stereocenters. Alpha-polyhalomethylcarbinols are generated with the simple and inexpensive dihalomethanes and trihalomethanes.

Entities:  

Year:  2008        PMID： 18181637     DOI： 10.1021/ol702825p

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


  8 in total

1.  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

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

Authors:  Susumu Oda; Hisashi Yamamoto
Journal:  Org Lett       Date:  2013-11-08       Impact factor: 6.005

3.  Super silyl stereo-directing groups for complete 1,5-syn and -anti stereoselectivities in the aldol reactions of beta-siloxy methyl ketones with aldehydes.

Authors:  Yousuke Yamaoka; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2010-04-21       Impact factor: 15.419

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

Authors:  Susumu Oda; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-21       Impact factor: 15.336

5.  A triple-aldol cascade reaction for the rapid assembly of polyketides.

Authors:  Brian J Albert; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-01       Impact factor: 15.336

6.  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

7.  Synthesis and purification of iodoaziridines involving quantitative selection of the optimal stationary phase for chromatography.

Authors:  Tom Boultwood; Dominic P Affron; James A Bull
Journal:  J Vis Exp       Date:  2014-05-16       Impact factor: 1.355

8.  Synthesis of cis-C-iodo-N-tosyl-aziridines using diiodomethyllithium: reaction optimization, product scope and stability, and a protocol for selection of stationary phase for chromatography.

Authors:  Tom Boultwood; Dominic P Affron; Aaron D Trowbridge; James A Bull
Journal:  J Org Chem       Date:  2013-06-18       Impact factor: 4.354
  8 in total

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