Literature DB >> 12074680

Practical and highly selective oxazolidinethione-based asymmetric acetate aldol reactions with aliphatic aldehydes.

Nathan R Guz1, Andrew J Phillips.   

Abstract

[reaction: see text] The utility of a valine-derived oxazolidinethione for auxiliary-based asymmetric acetate aldol reactions is reported. Titanium(IV) chloride, along with (-)-sparteine and N-methylpyrrolidinone, is employed for enolization. Subsequent aldol reaction with aliphatic aldehydes occurs with high diastereoselectivity (from 92:8 to 99:1 dr).

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Year:  2002        PMID： 12074680     DOI： 10.1021/ol026108w

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


  4 in total

1.  Unified synthesis of C19-C26 subunits of amphidinolides B1, B2, and B3 by exploiting unexpected stereochemical differences in Crimmins' and Evans' aldol reactions.

Authors:  Wei Zhang; Rich G Carter; Alexandre F T Yokochi
Journal:  J Org Chem       Date:  2004-04-02       Impact factor: 4.354

2.  Acetylphosphonate as a surrogate of acetate or acetamide in organocatalyzed enantioselective aldol reactions.

Authors:  Jie Guang; Qunsheng Guo; John Cong-Gui Zhao
Journal:  Org Lett       Date:  2012-05-31       Impact factor: 6.005

3.  Investigations into the use of a polyfluorooctanol as an auxiliary component for an aldol reaction.

Authors:  Jason Eames; Hasina Khanom
Journal:  Molecules       Date:  2004-04-30       Impact factor: 4.411

4.  Asymmetric Synthesis of Homocitric Acid Lactone.

Authors:  Leslie A Nickerson; Valerie Huynh; Edward I Balmond; Stephen P Cramer; Jared T Shaw
Journal:  J Org Chem       Date:  2016-10-21       Impact factor: 4.354
  4 in total

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