Literature DB >> 18616322

1,5-Asymmetric induction in boron-mediated aldol reactions of beta-alkoxy methylketones.

Luiz C Dias1, Anderson A de Marchi, Marco A B Ferreira, Andrea M Aguilar.   

Abstract

Good levels of substrate-controlled, 1,5- syn-stereoinduction are obtained in boron-mediated aldol reactions of beta-trichloromethyl-beta-alkoxy and beta-trifluoromethyl-beta-alkoxy methylketones with achiral aldehydes, independent of the nature of the beta-alkoxy protecting group (TBS or PMB). In the case of boron aldol reactions of beta-aryl-beta-alkoxy methylketones, the 1,5- anti-adducts were obtained with high levels of diastereoselectivity only with a beta-OPMB group.

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Year:  2008        PMID: 18616322     DOI: 10.1021/jo8009165

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


  3 in total

1.  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

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

Authors:  Patrick B Brady; Susumu Oda; Hisashi Yamamoto
Journal:  Org Lett       Date:  2014-07-15       Impact factor: 6.005

3.  Modifying electron transfer between photoredox and organocatalytic units via framework interpenetration for β-carbonyl functionalization.

Authors:  Zhengqiang Xia; Cheng He; Xiaoge Wang; Chunying Duan
Journal:  Nat Commun       Date:  2017-08-25       Impact factor: 14.919

  3 in total

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