Literature DB >> 19222172

A switch of facial selectivities using alpha-heteroatom-substituted aldehydes in the vinylogous Mukaiyama aldol reaction.

Mariko Shinoyama1, Shin-ichi Shirokawa, Atsuo Nakazaki, Susumu Kobayashi.   

Abstract

The vinylogous Mukaiyama aldol reaction (VMAR) of chiral nonracemic ketene silyl N,O-acetal with various aldehydes is demonstrated. VMAR with alpha-heteroatom-unsubstituted aldehydes proceeded with a high degree of anti-selectivity. In sharp contrast, moderate to high syn-selectivity was observed when alpha-heteroatom-substituted aldehydes were used.

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Year:  2009        PMID： 19222172     DOI： 10.1021/ol9000312

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


  4 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.  Re2 O7 -Mediated Dehydrative Cyclization Reactions: Total Synthesis of Herboxidiene and Its 12-Desmethyl Analogue.

Authors:  Tyler M Rohrs; Qi Qin; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-28       Impact factor: 15.336

3.  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

Review 4.  Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis.

Authors:  Martin Cordes; Markus Kalesse
Journal:  Molecules       Date:  2019-08-22       Impact factor: 4.411
  4 in total

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