Literature DB >> 18831554

L-selectride-mediated highly diastereoselective asymmetric reductive aldol reaction: access to an important subunit for bioactive molecules.

Arun K Ghosh1, Jorden Kass, David D Anderson, Xiaoming Xu, Christine Marian.   

Abstract

L-selectride reduction of a chiral or achiral enone followed by reaction of the resulting enolate with optically active alpha-alkoxy aldehydes proceeded with excellent diastereoselectivity. The resulting alpha,alpha-dimethyl-beta-hydroxy ketones are inherent to a variety of biologically active natural products.

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Year:  2008        PMID： 18831554      PMCID： PMC2943828          DOI： 10.1021/ol801971t

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


  15 in total

1.  Diastereoselective cobalt-catalyzed aldol and Michael cycloreductions.

Authors:  T G Baik; A L Luis; L C Wang; M J Krische
Journal:  J Am Chem Soc       Date:  2001-05-30       Impact factor: 15.419

2.  Toward the total synthesis of natural peloruside a: stereoselective synthesis of the backbone of the core.

Authors:  Bo Liu; Wei-Shan Zhou
Journal:  Org Lett       Date:  2004-01-08       Impact factor: 6.005

3.  A three-component tandem reductive aldol reaction catalyzed by N-heterocyclic carbene-copper complexes.

Authors:  Alexandre Welle; Silvia Díez-González; Bernard Tinant; Steven P Nolan; Olivier Riant
Journal:  Org Lett       Date:  2006-12-21       Impact factor: 6.005

4.  Highly diastereo- and enantioselective copper-catalyzed domino reduction/aldol reaction of ketones with methyl acrylate.

Authors:  Julia Deschamp; Olivier Chuzel; Jérôme Hannedouche; Olivier Riant
Journal:  Angew Chem Int Ed Engl       Date:  2006-02-13       Impact factor: 15.336

5.  Asymmetric induction in hydrogen-mediated reductive aldol additions to alpha-amino aldehydes catalyzed by rhodium: selective formation of syn-stereotriads directed by intramolecular hydrogen-bonding.

Authors:  Cheol-Kyu Jung; Michael J Krische
Journal:  J Am Chem Soc       Date:  2006-12-27       Impact factor: 15.419

6.  Epothilons A and B: antifungal and cytotoxic compounds from Sorangium cellulosum (Myxobacteria). Production, physico-chemical and biological properties.

Authors:  K Gerth; N Bedorf; G Höfle; H Irschik; H Reichenbach
Journal:  J Antibiot (Tokyo)       Date:  1996-06       Impact factor: 2.649

7.  Surprising role of aryl halides in nickel-catalyzed reductive aldol reactions.

Authors:  Christa C Chrovian; John Montgomery
Journal:  Org Lett       Date:  2007-02-01       Impact factor: 6.005

8.  Intermolecular asymmetric reductive aldol reaction of ketones as acceptors promoted by chiral Rh(Phebox) catalyst.

Authors:  Takushi Shiomi; Hisao Nishiyama
Journal:  Org Lett       Date:  2007-03-27       Impact factor: 6.005

9.  Peloruside A: a potent cytotoxic macrolide isolated from the new zealand marine sponge Mycale sp.

Authors:  L M West; P T Northcote; C N Battershill
Journal:  J Org Chem       Date:  2000-01-28       Impact factor: 4.354

10.  Reductive aldol coupling of divinyl ketones via rhodium-catalyzed hydrogenation: syn-diastereoselective construction of beta-hydroxyenones.

Authors:  Soo Bong Han; Michael J Krische
Journal:  Org Lett       Date:  2006-11-23       Impact factor: 6.005
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  7 in total

1.  Generation of stereochemically defined tetrasubstituted enolborinates by 1,4-hydroboration of α,β-unsaturated morpholine carboxamides with (diisopinocampheyl)borane.

Authors:  Christophe Allais; Andy S Tsai; Philippe Nuhant; William R Roush
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-15       Impact factor: 15.336

2.  (Diisopinocampheyl)borane-mediated reductive aldol reactions of acrylate esters: enantioselective synthesis of anti-aldols.

Authors:  Christophe Allais; Philippe Nuhant; William R Roush
Journal:  Org Lett       Date:  2013-07-25       Impact factor: 6.005

3.  Synthesis of Bioactive Natural Products by Asymmetric syn- and anti-Aldol Reactions.

Authors:  Arun K Ghosh; Zachary L Dawson
Journal:  Synthesis (Stuttg)       Date:  2009-09       Impact factor: 3.157

4.  Capturing the essence of organic synthesis: from bioactive natural products to designed molecules in today's medicine.

Authors:  Arun K Ghosh
Journal:  J Org Chem       Date:  2010-10-11       Impact factor: 4.354

5.  Peloruside B, a potent antitumor macrolide from the New Zealand marine sponge Mycale hentscheli: isolation, structure, total synthesis, and bioactivity.

Authors:  A Jonathan Singh; Chun-Xiao Xu; Xiaoming Xu; Lyndon M West; Anja Wilmes; Ariane Chan; Ernest Hamel; John H Miller; Peter T Northcote; Arun K Ghosh
Journal:  J Org Chem       Date:  2010-01-01       Impact factor: 4.354

6.  Catalytic Reductive Aldol and Mannich Reactions of Enone, Acrylate, and Vinyl Heteroaromatic Pronucleophiles.

Authors:  Cole C Meyer; Eliezer Ortiz; Michael J Krische
Journal:  Chem Rev       Date:  2020-03-19       Impact factor: 60.622

7.  Diisopinocampheylborane-mediated reductive aldol reactions: highly enantio- and diastereoselective synthesis of syn aldols from N-acryloylmorpholine.

Authors:  Philippe Nuhant; Christophe Allais; William R Roush
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-01       Impact factor: 15.336
  7 in total

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