Literature DB >> 19472247

1,n-glycols as dialdehyde equivalents in iridium-catalyzed enantioselective carbonyl allylation and iterative two-directional assembly of 1,3-polyols.

Yu Lu1, In Su Kim, Abbas Hassan, David J Del Valle, Michael J Krische.   

Abstract

Unstable? We're able! 1,n-Glycols serve as synthetic equivalents to unstable dialdehydes in two-directional carbonyl allylation from the alcohol oxidation level under iridium-catalyzed transfer hydrogenation conditions. Iterative asymmetric allylation employing 1,3-propanediol enables the rapid assembly of protected 1,3-polyol substructures with exceptional levels of stereocontrol.

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Year:  2009        PMID： 19472247      PMCID： PMC2843750          DOI： 10.1002/anie.200901648

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  47 in total

1.  Enantioselective allyltitanation. Efficient synthesis of the C1-C14 polyol subunit of amphotericin B.

Authors:  S BouzBouz; J Cossy
Journal:  Org Lett       Date:  2000-12-14       Impact factor: 6.005

2.  Total synthesis of (+)-strictifolione.

Authors:  Samir BouzBouz; Janine Cossy
Journal:  Org Lett       Date:  2003-05-29       Impact factor: 6.005

3.  Enantioselective catalytic allylation of carbonyl groups by umpolung of pi-allyl palladium complexes.

Authors:  Giuseppe Zanoni; Serafino Gladiali; Alberto Marchetti; Paolo Piccinini; Ilenia Tredici; Giovanni Vidari
Journal:  Angew Chem Int Ed Engl       Date:  2004-02-06       Impact factor: 15.336

4.  Hydrogen-mediated C-C bond formation: a broad new concept in catalytic C-C coupling.

Authors:  Ming-Yu Ngai; Jong-Rock Kong; Michael J Krische
Journal:  J Org Chem       Date:  2007-02-16       Impact factor: 4.354

5.  Iterative Cr-mediated catalytic asymmetric allylation to synthesize syn/syn- and anti/anti-1,3,5-triols.

Authors:  Zhiyu Zhang; Sylvain Aubry; Yoshito Kishi
Journal:  Org Lett       Date:  2008-06-13       Impact factor: 6.005

6.  Total synthesis of (+)-neopeltolide.

Authors:  Haruhiko Fuwa; Shinya Naito; Tomomi Goto; Makoto Sasaki
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

7.  Total synthesis of marinomycins A-C and of their monomeric counterparts monomarinomycin A and iso-monomarinomycin A.

Authors:  K C Nicolaou; Andrea L Nold; Robert R Milburn; Corinna S Schindler; Kevin P Cole; Junichiro Yamaguchi
Journal:  J Am Chem Soc       Date:  2007-01-24       Impact factor: 15.419

8.  An efficient and stereoselective synthesis of the monomeric counterpart of marinomycin A.

Authors:  Dominique Amans; Véronique Bellosta; Janine Cossy
Journal:  Org Lett       Date:  2007-03-14       Impact factor: 6.005

9.  Catalyst-directed diastereoselectivity in hydrogenative couplings of acetylene to alpha-chiral aldehydes: formal synthesis of all eight L-hexoses.

Authors:  Soo Bong Han; Jong Rock Kong; Michael J Krische
Journal:  Org Lett       Date:  2008-08-26       Impact factor: 6.005

10.  Total synthesis of the polyene-polyol macrolide RK-397, featuring cross-couplings of alkynylepoxide modules.

Authors:  Svetlana A Burova; Frank E McDonald
Journal:  J Am Chem Soc       Date:  2004-03-03       Impact factor: 15.419
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  45 in total

1.  Alkyne-aldehyde reductive C-C coupling through ruthenium-catalyzed transfer hydrogenation: direct regio- and stereoselective carbonyl vinylation to form trisubstituted allylic alcohols in the absence of premetallated reagents.

Authors:  Joyce C Leung; Ryan L Patman; Brannon Sam; Michael J Krische
Journal:  Chemistry       Date:  2011-09-27       Impact factor: 5.236

2.  Ruthenium(0) Catalyzed Endiyne-α-Ketol [4 + 2] Cycloaddition: Convergent Assembly of Type II Polyketide Substructures via C-C Bond Forming Transfer Hydrogenation.

Authors:  Aakarsh Saxena; Felix Perez; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-05-04       Impact factor: 15.419

Review 3.  Asymmetric Iridium-Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition.

Authors:  Inji Shin; Michael J Krische
Journal:  Top Curr Chem       Date:  2016

4.  Direct generation of acyclic polypropionate stereopolyads via double diastereo- and enantioselective iridium-catalyzed crotylation of 1,3-diols: beyond stepwise carbonyl addition in polyketide construction.

Authors:  Xin Gao; Hoon Han; Michael J Krische
Journal:  J Am Chem Soc       Date:  2011-07-25       Impact factor: 15.419

5.  Consecutive iridium catalyzed C-C and C-H bond forming hydrogenations for the diastereo- and enantioselective synthesis of syn-3-fluoro-1-alcohols: C-H (2-fluoro)allylation of primary alcohols.

Authors:  Abbas Hassan; T Patrick Montgomery; Michael J Krische
Journal:  Chem Commun (Camb)       Date:  2012-04-04       Impact factor: 6.222

6.  Protecting-group-free synthesis of 3-tert-prenylated oxindoles: contiguous all-carbon quaternary centers via tertiary neopentyl substitution.

Authors:  Christopher D Grant; Michael J Krische
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005

7.  Asymmetric alcohol C-H allylation and syn-crotylation: C9-C20 of tetrafibricin.

Authors:  Takahiko Itoh; T Patrick Montgomery; Antonio Recio; Michael J Krische
Journal:  Org Lett       Date:  2014-01-14       Impact factor: 6.005

8.  Diastereo- and enantioselective anti-alkoxyallylation employing allylic gem-dicarboxylates as allyl donors via iridium-catalyzed transfer hydrogenation.

Authors:  Soo Bong Han; Hoon Han; Michael J Krische
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419

9.  Studies toward the unique pederin family member psymberin: full structure elucidation, two alternative total syntheses, and analogs.

Authors:  Yu Feng; Xin Jiang; Jef K De Brabander
Journal:  J Am Chem Soc       Date:  2012-10-04       Impact factor: 15.419

10.  Evaluation of Chromane-Based Bryostatin Analogues Prepared via Hydrogen-Mediated C-C Bond Formation: Potency Does Not Confer Bryostatin-like Biology.

Authors:  John M Ketcham; Ivan Volchkov; Te-Yu Chen; Peter M Blumberg; Noemi Kedei; Nancy E Lewin; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-09-27       Impact factor: 15.419
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